CN107540597A - The preparation method of the ketone derivatives of N dimethylacetamide bases indoles 2 - Google Patents
The preparation method of the ketone derivatives of N dimethylacetamide bases indoles 2 Download PDFInfo
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Abstract
The present invention relates to a kind of preparation method of the ketone derivatives of N dimethylacetamides base indoles 2, comprise the following steps：By the substitution N dimethylacetamide base phenyl acetamide derivatives and iodobenzene diacetate of formula (1) in the presence of palladium salt catalyst, reacted in organic solvent at 25 80 DEG C, obtain the ketone derivatives of N dimethylacetamide bases indoles 2 of formula (2)：R1、R2、R3、R4、R5、R6Independently selected from hydrogen, alkyl, alkoxy, acetoxyl group, halogen or trifluoromethyl.The method raw material of the present invention is easy to get, high income, reaction condition is gentle, universality is good and green.
Description
Technical field
The present invention relates to organic synthesis field, more particularly to a kind of system of N- dimethylacetamides base indol-2-one derivates
Preparation Method.
Background technology
Indol-2-one derivates generally have significant bioactivity and pharmacological activity, such as treating tuberculosis, anticonvulsion, anti-height
Blood glucose and anti-vibrios, therefore synthesis of indole -2- ketone derivatives have important value.
So far, the synthetic method of indol-2-one derivates mainly has following several：
SU841264, a kind of synthetic method of indol-2-one derivates is disclosed in 1995, this method route is longer, always
Yield is relatively low.
Using bromophenyl acetic acid it is Material synthesis indol-2-one derivates method, and the N hydrocarbylations of indol-2-one
Method, respectively in WO/2004/087658A1,2004 and Organic Process Research＆Development.2009,
The shortcomings that open on 13,443-449, but these methods are respectively provided with step length, and yield is low, and cost is high.
In a word, prior art prepares during indol-2-one derivates yield be present relatively low, expensive starting materials, reaction condition
It is harsh and to environment it is unfriendly the deficiencies of.Therefore, from c h bond activation, exploitation reaction condition is gentle, it is applied widely,
The synthetic method for meeting Green Chemistry requirement is extremely important.
The content of the invention
In order to solve the above technical problems, it is an object of the invention to provide a kind of N- dimethylacetamides base indol-2-one derivative
The preparation method of thing, method raw material of the invention is easy to get, high income, reaction condition is gentle, universality is good and green.
The invention provides a kind of preparation method of N- dimethylacetamides base indol-2-one derivates, it is characterised in that bag
Include following steps：
By substitution N- dimethylacetamide base phenyl acetamide derivatives and the iodobenzene diacetate (PhI (OAc) of formula (1)2) in palladium
In the presence of salt catalyst, reacted in organic solvent at 25-80 DEG C, obtain the N- dimethylacetamide base indoles -2- of formula (2)
Ketone derivatives：
Wherein, R1、R2、R3、R4、R5、R6Independently selected from hydrogen, alkyl, alkoxy, acetoxyl group, halogen, aromatic radical or three
Methyl fluoride.Wherein, R5Another substituted radical on the carbon atom connected is hydrogen or methyl.
Further, R1、R2、R3、R4、R5、R6It is hydrogen；
Or R1、R2、R3、R4One of which be alkyl, alkoxy, aromatic radical, halogen or trifluoromethyl, other threes are equal
For hydrogen, R5、R6It is hydrogen；
Or R1、R2、R4、R5It is hydrogen, R3For alkyl or aromatic radical, R6For C1-C6Alkyl；
Or R4、R6It is hydrogen, R5For alkyl or acetoxyl group, R1、R2Or R3In one of which be alkyl, aromatic radical or halogen
Element, other are both at hydrogen.
Further, alkyl C1-C6Alkyl.Preferably, alkyl is methyl, ethyl, butyl, isopropyl, butyl, ring fourth
Base or cyclohexyl.
Further, alkoxy C1-C6Alkoxy.Preferably, alkoxy is methoxyl group.
Further, aromatic radical is phenyl.
Further, halogen is chlorine, bromine or iodine.
Further, palladium salt catalyst is palladium (Pd (OAc)2) or palladium bichloride.Preferably, palladium salt catalyst is acetic acid
Palladium.
Further, organic solvent is toluene, 1,2- dichloroethanes (DCE), tetrahydrofuran (THF), Isosorbide-5-Nitrae-dioxane
Or acetic anhydride.Preferably, organic solvent is toluene.
Further, rubbing for N- dimethylacetamide bases phenyl acetamide derivative, iodobenzene diacetate and palladium salt catalyst is substituted
You are than being 1:1-2:0.05-0.1.Preferably, N- dimethylacetamide bases phenyl acetamide derivative, iodobenzene diacetate and palladium salt are substituted
The mol ratio of catalyst is 1:1.5:0.05.
Preferably, reaction temperature is 60 DEG C.
By such scheme, the present invention at least has advantages below：
1. the present invention is starting material using substitution N- dimethylacetamides-phenyl acetamide derivative derivative, raw material is easy to get, planted
Class is various；The product types that profit is obtained by the present invention are various, not only can directly using but also to can be used for other further
Reaction.
2. reaction condition of the present invention is gentle, operation and last handling process are simple, yield is very high, is suitable for scale life
Production.
Described above is only the general introduction of technical solution of the present invention, in order to better understand the technological means of the present invention,
And can be practiced according to the content of specification, below with presently preferred embodiments of the present invention and coordinate detailed description as after.
Embodiment
With reference to embodiment, the embodiment of the present invention is described in further detail.Following examples are used for
Illustrate the present invention, but be not limited to the scope of the present invention.Me in below equation represents methyl (CH3)。
The synthesis of embodiment 1N- dimethylacetamide base indol-2-ones
(1) N- dimethylacetamide base phenyl acetamide 1a (0.0440g, 0.2mmol) are weighed, palladium (0.0022g,
0.01mmol) it is dissolved in 1mL toluene, adds PhI (OAc)2(0.0966g, 0.3mmol).Mixture is heated to 60 DEG C, TLC with
Track reaction is fully completed until reaction.Reaction terminates rear crude on silica gel column chromatography for separation (petroleum ether:Ethyl acetate=1:2)
Compound 2a is obtained after purification.It is 86% to separate yield.
(2) N- dimethylacetamide base phenyl acetamide 1a (0.0440g, 0.2mmol) are weighed, palladium (0.0022g,
0.01mmol) it is dissolved in 1mL toluene, adds PhI (OAc)2(0.0966g, 0.3mmol).Mixture is heated to 80 DEG C, TLC with
Track reaction is fully completed until reaction.Reaction terminates rear crude on silica gel column chromatography for separation (petroleum ether:Ethyl acetate=1:2)
Compound 2a is obtained after purification.It is 83% to separate yield.
(3) N- dimethylacetamide base phenyl acetamide 1a (0.0440g, 0.2mmol) are weighed, palladium (0.0022g,
0.01mmol) it is dissolved in 1mL toluene, adds PhI (OAc)2(0.0966g, 0.3mmol).Mixture 25 DEG C reaction, TLC with
Track reaction is fully completed until reaction.Reaction terminates rear crude on silica gel column chromatography for separation (petroleum ether:Ethyl acetate=1:2)
Compound 2a is obtained after purification.It is 53% to separate yield.
(4) (2) weigh N- dimethylacetamide base phenyl acetamide 1a (0.0440g, 0.2mmol), palladium (0.0022g,
0.01mmol) it is dissolved in 1mL 1, in 2- dichloroethanes (DCE), adds PhI (OAc)2(0.0966g, 0.3mmol).Mixture adds
To 80 DEG C, TLC tracking reaction is fully completed heat until reaction.Reaction terminates rear crude on silica gel column chromatography for separation (petroleum ether:
Ethyl acetate=1:2) compound 2a is obtained after purifying.It is 67% to separate yield.
(5) N- dimethylacetamide base phenyl acetamide 1a (0.0440g, 0.2mmol) are weighed, palladium (0.0022g,
0.01mmol) it is dissolved in 1mL tetrahydrofurans (THF), adds PhI (OAc)2(0.0966g, 0.3mmol).Mixture is heated to 80
DEG C, TLC tracking reaction is fully completed until reaction.Reaction terminates rear crude on silica gel column chromatography for separation (petroleum ether:Acetic acid second
Ester=1:2) compound 2a is obtained after purifying.It is 22% to separate yield.
(6) N- dimethylacetamide base phenyl acetamide 1a (0.0440g, 0.2mmol) are weighed, palladium (0.0022g,
0.01mmol) it is dissolved in 1mL1, in 4- dioxane, adds PhI (OAc)2(0.0966g, 0.3mmol).Mixture is heated to 80
DEG C, TLC tracking reaction is fully completed until reaction.Reaction terminates rear crude on silica gel column chromatography for separation (petroleum ether:Acetic acid second
Ester=1:2) compound 2a is obtained after purifying.It is 45% to separate yield.
(7) N- dimethylacetamide base phenyl acetamide 1a (0.0440g, 0.2mmol) are weighed, palladium (0.0022g,
0.01mmol) it is dissolved in 1mL acetic anhydride, adds PhI (OAc)2(0.0966g, 0.3mmol).Mixture is heated to 80 DEG C, TLC
Tracking reaction is fully completed until reaction.Reaction terminates rear crude on silica gel column chromatography for separation (petroleum ether:Ethyl acetate=1:
2) compound 2a is obtained after purifying.It is 17% to separate yield.Nuclear-magnetism and mass spectral analysis are carried out to above-mentioned product, it is as a result as follows：
2a:1H NMR(400MHz,CDCl3) δ 7.26-7.21 (m, 2H), 7.04-7.00 (m, 1H), 6.80 (d, J=
7.60Hz,1H),4.51(s,2H),3.59(s,2H),3.11(s,3H),2.96(s,3H)；13C NMR(101MHz,CDCl3)δδ
175.30,166.16,144.52,128.00,124.46,124.28,122.64,108.99,41.88,36.72,35.92,
35.71；HRMS(ESI-TOF)m/z calcd for C12H14N2O2[M+H]+:219.1134,Found:219.1123.
Embodiment two：The synthesis of 6- methoxy-N-acetyl dimethylamino indol-2-ones
Weigh 4- methoxy-N-acetyl dimethylamino phenyl acetamide 1b (0.0500g, 0.2mmol), palladium
(0.0022g, 0.01mmol) is dissolved in 1mL toluene (toluene), adds PhI (OAc)2(0.0966g, 0.3mmol).Mixing
Thing is heated to 60 DEG C, and TLC tracking reaction is fully completed until reaction.Reaction terminates rear crude on silica gel column chromatography for separation (stone
Oily ether:Ethyl acetate=1:2) compound 2b is obtained after purifying.It is 91% to separate yield.Nuclear-magnetism and mass spectrum point are carried out to product
Analysis, it is as a result as follows：
2b:1H NMR(400MHz,CDCl3) δ 7.12 (d, J=8.40Hz, 1H), 6.53 (d, J=8.00Hz, 1H), 6.42
(s,1H),4.49(s,2H),3.79(s,3H),3.53(s,2H),3.11(s,3H),2.97(s,3H)；13C NMR(101MHz,
CDCl3)δ176.18,166.18,160.23,145.83,125.06,116.26,106.80,97.21,55.77,42.09,
36.86,36.07,35.26；HRMS Calcd for C13H16N2O3[M+H]+:249.1239,Found:249.1242.
Embodiment three：The synthesis of 6- methyl-N- dimethylacetamide base indol-2-ones
Weigh 4- methyl-N- dimethylacetamide base phenyl acetamide 1c (0.0468g, 0.2mmol), palladium (0.0022g,
0.01mmol) it is dissolved in 1mL toluene, adds PhI (OAc)2(0.0966g, 0.3mmol).Mixture is heated to 60 DEG C, TLC with
Track reaction is fully completed until reaction.Reaction terminates rear crude on silica gel column chromatography for separation (petroleum ether:Ethyl acetate=1:2)
Compound 2c is obtained after purification.It is 88% to separate yield.
2c:1H NMR(400MHz,CDCl3) δ 7.11 (d, J=7.60Hz, 1H), 6.83 (d, J=7.60Hz, 1H), 6.63
(s,1H),4.50(s,2H),3.55(s,2H),3.12(s,3H),2.98(s,3H),2.34(s,3H).；13C NMR(101MHz,
CDCl3)δ175.81,166.37,144.73,138.18,124.30,123.35,121.37,109.94,42.03,36.86,
36.07,35.60,22.02；HRMS Calcd for C13H16N2O2[M+H]+:233.1290,Found:233.1297.
Example IV：The synthesis of 6- trifluoromethyl-N- dimethylacetamide base indol-2-ones
Weigh 4- trifluoromethyl-N- dimethylacetamide base phenyl acetamide 1d (0.0576g, 0.2mmol), palladium
(0.0022g, 0.01mmol) is dissolved in 1mL toluene, adds PhI (OAc)2(0.0966g, 0.3mmol).Mixture is heated to 60
DEG C, TLC tracking reaction is fully completed until reaction.Reaction terminates rear crude on silica gel column chromatography for separation (petroleum ether:Acetic acid second
Ester=1:2) compound 2d is obtained after purifying.It is 54% to separate yield.
2d:1H NMR(400MHz,CDCl3) δ 7.35-7.29 (dd, J=17.60,9.60Hz, 2H), 6.96 (s, 1H),
4.53(s,2H),3.64(s,2H),3.14(s,3H),2.98(s,3H)；13C NMR(101MHz,CDCl3)δ175.00,
165.54,145.32,130.63(q,JC-F=32.33Hz), 128.38,124.78,124.24 (q, JC-F=243.00Hz),
119.78(q,JC-F=4.00Hz), 105.70 (q, JC-F=3.67Hz), 41.77,36.71,36.05,35.64；19F NMR
(376MHz,CDCl3)δ-62.22；HRMS Calcd for C13H13F3N2O2[M+H]+:287.1007,Found:287.0998.
Embodiment five：The synthesis of the bromo- N- dimethylacetamides base indol-2-ones of 6-
Weigh the bromo- N- dimethylacetamides base phenyl acetamide 1e (0.0596g, 0.2mmol) of 4-, palladium (0.0022g,
0.01mmol) it is dissolved in 1mL toluene, adds PhI (OAc)2(0.0966g, 0.3mmol).Mixture is heated to 60 DEG C, TLC with
Track reaction is fully completed until reaction.Reaction terminates rear crude on silica gel column chromatography for separation (petroleum ether:Ethyl acetate=1:2)
Compound 2e is obtained after purification.It is 63% to separate yield.
2e:1H NMR(400MHz,CDCl3) δ 7.3 (s, 1H), 7.36 (d, J=8.40Hz, 1H), 6.69 (d, J=
8.00Hz,1H),4.50(s,2H),3.60(s,2H),3.11(s,3H),2.97(s,3H)；13C NMR(101MHz,CDCl3)δ
174.69,165.93,143.79,131.00,127.78,126.41,115.40,110.60,41.99,36.84,36.06,
35.65；HRMS Calcd for C13H13BrN2O2[M+H]+:297.0239,Found:297.0225.
Embodiment six：The synthesis of 6- phenyl-N- dimethylacetamide base indol-2-ones
Weigh 4- phenyl-N- dimethylacetamide base phenyl acetamide 1f (0.0582g, 0.2mmol), palladium (0.0022g,
0.01mmol) it is dissolved in 1mL toluene, adds PhI (OAc)2(0.0966g, 0.3mmol).Mixture is heated to 60 DEG C, TLC with
Track reaction is fully completed until reaction.Reaction terminates rear crude on silica gel column chromatography for separation (petroleum ether:Ethyl acetate=1:2)
Compound 2f is obtained after purification.It is 78% to separate yield.
2f:1H NMR(400MHz,CDCl3) δ 7.56 (d, J=6.80Hz, 2H), 7.44-7.41 (m, 2H), 7.35 (d, J
=7.60Hz, 1H), 7.30 (d, J=7.60Hz, 1H), 7.25 (d, J=8.00Hz, 1H), 6.99 (s, 1H), 4.56 (s, 2H),
3.63(s,2H),3.13(s,3H),2.97(s,3H)；13C NMR(101MHz,CDCl3)δ175.63,166.13,145.22,
141.74,141.37,128.93,127.63,127.50,124.77,123.46,121.82,108.02,42.01,36.82,
36.05,35.63；HRMS Calcd for C18H18N2O2[M+H]+:295.1447,Found:295.1436.
Embodiment seven：The synthesis of the chloro- N- dimethylacetamides base indol-2-ones of 6-
Weigh the chloro- N- dimethylacetamides base phenyl acetamide 1g (0.0508g, 0.2mmol) of 4-, palladium (0.0022g,
0.01mmol) it is dissolved in 1mL toluene, adds PhI (OAc)2(0.0966g, 0.3mmol).Mixture is heated to 60 DEG C, TLC with
Track reaction is fully completed until reaction.Reaction terminates rear crude on silica gel column chromatography for separation (petroleum ether:Ethyl acetate=1:2)
Compound 2g is obtained after purification.It is 73% to separate yield.
2g:1H NMR(400MHz,CDCl3) δ 7.14 (d, J=7.9Hz, 1H), 6.98 (d, J=9.7Hz, 1H), 6.76
(s,1H),4.47(s,2H),3.55(s,2H),3.11(s,3H),2.97(s,3H)；13C NMR(101MHz,CDCl3)δ
175.37(s),165.70(s),145.85(s),133.85(s),125.42(s),122.72(s),122.60(s),109.74
(s),41.82(s),36.73(s),36.05(s),35.36(s)；HRMS Calcd for C12H13ClN2O2[M+H]+:
253.0666,Found:253.0660.
Embodiment eight：The synthesis of the iodo- N- dimethylacetamides base indol-2-ones of 5-
Weigh the iodo- N- dimethylacetamides base phenyl acetamide 1h (0.0672g, 0.2mmol) of 3-, palladium (0.0022g,
0.01mmol) it is dissolved in 1mL toluene, adds PhI (OAc)2(0.0966g, 0.3mmol).Mixture is heated to 60 DEG C, TLC with
Track reaction is fully completed until reaction.Reaction terminates rear crude on silica gel column chromatography for separation (petroleum ether:Ethyl acetate=1:2)
Compound 2h is obtained after purification.It is 56% to separate yield.
2h:1H NMR(400MHz,CDCl3) δ 7.54 (s, 2H), 6.59 (d, J=8.00Hz, 1H), 4.49 (s, 2H),
3.58(s,2H),3.11(s,3H),2.96(s,3H)；13C NMR(101MHz,CDCl3)δ170.28,167.90,138.38,
137.20,136.55,130.68,128.76,94.91,43.04,41.65,36.08,35.77；HRMS Calcd for
C12H13IN2O2[M+H+]:345.0022,Found:345.0010.
Embodiment nine：The synthesis of 5- trifluoromethyl-N- dimethylacetamide base indol-2-ones
Weigh 3- trifluoromethyl-N- dimethylacetamide base phenyl acetamide 1i (0.0576g, 0.2mmol), palladium
(0.0022g, 0.01mmol) is dissolved in 1mL toluene, adds PhI (OAc)2(0.0966g, 0.3mmol).Mixture is heated to 60
DEG C, TLC tracking reaction is fully completed until reaction.Reaction terminates rear crude on silica gel column chromatography for separation (petroleum ether:Acetic acid second
Ester=1:2) compound 2i is obtained after purifying.It is 58% to separate yield.
2i:1H NMR(400MHz,CDCl3) δ 7.52 (d, J=9.00Hz, 1H), 7.50 (s, 1H), 6.86 (d, J=
8.00Hz,1H),4.55(s,2H),3.65(s,2H),3.14(s,3H),2.98(s,3H)；13C NMR(101MHz,CDCl3)δ
175.12,165.73,147.68,135.63(q,JC-F=34.33Hz), 125.94 (q, JC-F=4.33Hz), 123.24 (q,
JC-F=286.12Hz), 124.89,121.73 (q, JC-F=4.00Hz), 108.93,41.90,36.82,36.08,35.56；
HRMS Calcd for C13H13F3N2O2[M+H]+:287.1007,Found:287.0999.
Embodiment ten：The synthesis of the bromo- N- dimethylacetamides base indol-2-ones of 5-
Weigh the bromo- N- dimethylacetamides base phenyl acetamide 1j (0.0596g, 0.2mmol) of 3-, palladium (0.0022g,
0.01mmol) it is dissolved in 1mL toluene, adds PhI (OAc)2(0.0966g, 0.3mmol).Mixture is heated to 60 DEG C, TLC with
Track reaction is fully completed until reaction.Reaction terminates rear crude on silica gel column chromatography for separation (petroleum ether:Ethyl acetate=1:2)
Compound 2j is obtained after purification.It is 62% to separate yield.
2j:1H NMR(400MHz,CDCl3) δ 7.37 (s, 1H), 7.36 (d, J=7.60Hz, 1H), 6.69 (d, J=
8.40Hz,1H),4.50(s,2H),3.60(s,2H),3.12(s,3H),2.97(s,3H)；13C NMR(101MHz,CDCl3)δ
174.69,165.93,143.79,131.00,127.78,126.41,115.40,110.60,41.99,36.84,36.06,
35.65；HRMS Calcd for C12H13BrN2O2[M+H]+:297.0239,Found:297.0229.
Embodiment 11：The synthesis of the chloro- N- dimethylacetamides base indol-2-ones of 5-
Weigh the chloro- N- dimethylacetamides base phenyl acetamide 1k (0.0508g, 0.2mmol) of 3-, palladium (0.0022g,
0.01mmol) it is dissolved in 1mL toluene, adds PhI (OAc)2(0.0966g, 0.3mmol).Mixture is heated to 60 DEG C, TLC with
Track reaction is fully completed until reaction.Reaction terminates rear crude on silica gel column chromatography for separation (petroleum ether:Ethyl acetate=1:2)
Compound 2k is obtained after purification.It is 70% to separate yield.
2k:1H NMR(400MHz,CDCl3) δ 7.23 (s, 1H), 7.21 (d, J=11.60Hz, 1H), 6.72 (d, J=
8.00Hz,1H),4.50(s,2H),3.59(s,2H),3.11(s,3H),2.97(s,3H)；13C NMR(101MHz,CDCl3)δ
174.82,165.97,143.28,128.07,126.01,125.02,110.07,41.99,36.83,36.04,35.73；HRMS
Calcd for C12H13ClN2O2[M+H]+:253.0666,Found:253.0650.
Embodiment 12：The synthesis of 4- methoxy-N-acetyl dimethylamino indol-2-ones
Weigh 2- methoxy-N-acetyl dimethylamino phenyl acetamide 1l (0.0500g, 0.2mmol), palladium
(0.0022g, 0.01mmol) is dissolved in 1mL toluene, adds PhI (OAc)2(0.0966g, 0.3mmol).Mixture is heated to 60
DEG C, TLC tracking reaction is fully completed until reaction.Reaction terminates rear crude on silica gel column chromatography for separation (petroleum ether:Acetic acid second
Ester=1:2) compound 2l is obtained after purifying.It is 85% to separate yield.
2l:1H NMR(400MHz,CDCl3) δ 7.23-7.19 (m, 1H), 6.60 (d, J=8.40Hz, 1H), 6.49 (d, J
=4.00Hz, 1H), 4.50 (s, 2H), 3.85 (s, 3H), 3.52 (s, 2H), 3.10 (s, 3H), 2.97 (s, 3H)；13C NMR
(101MHz,CDCl3)δ175.72,166.41,145.81,129.43,111.12,105.81,102.55,55.68,42.30,
36.86,36.06,33.56；HRMS Calcd for C13H16N2O3[M+H]+:249.1239,Found:249.1236.
Embodiment 13：The synthesis of the bromo- N- dimethylacetamides base indol-2-ones of 4-
Weigh the bromo- N- dimethylacetamides base phenyl acetamide 1m (0.0596g, 0.2mmol) of 2-, palladium (0.0022g,
0.01mmol) it is dissolved in 1mL toluene, adds PhI (OAc)2(0.0966g, 0.3mmol).Mixture is heated to 60 DEG C, TLC with
Track reaction is fully completed until reaction.Reaction terminates rear crude on silica gel column chromatography for separation (petroleum ether:Ethyl acetate=1:2)
Compound 2m is obtained after purification.It is 57% to separate yield.
2m:1H NMR(400MHz,CDCl3) δ 7.18 (d, J=7.20Hz, 1H), 7.15-7.11 (m, 1H), 6.76 (d, J
=7.60Hz, 1H), 4.52 (s, 2H), 3.57 (s, 2H), 3.13 (s, 3H), 2.99 (s, 3H)；13C NMR(101MHz,CDCl3)
δ174.04,165.87,145.54,129.63,125.61,125.31,119.18,107.93,42.07,37.11,36.76,
35.99；HRMS Calcd for C12H13BrN2O2[M+H]+:297.0239,Found:297.0223.
Embodiment 14：The synthesis of the iodo- N- dimethylacetamides base indol-2-ones of 4-
Weigh the iodo- N- dimethylacetamides base phenyl acetamide 1n (0.0692g, 0.2mmol) of 2-, palladium (0.0022g,
0.01mmol) it is dissolved in 1mL toluene, adds PhI (OAc)2(0.0966g, 0.3mmol).Mixture is heated to 60 DEG C, TLC with
Track reaction is fully completed until reaction.Reaction terminates rear crude on silica gel column chromatography for separation (petroleum ether:Ethyl acetate=1:2)
Compound 2n is obtained after purification.It is 55% to separate yield.
2n:1H NMR(400MHz,CDCl3) δ 7.38 (d, J=8.00Hz, 1H), 6.99-6.95 (m, 1H), 6.77 (d, J
=7.60Hz, 1H), 4.48 (s, 2H), 3.48 (s, 2H), 3.12 (s, 3H), 2.97 (s, 3H)；13C NMR(101MHz,
CDCl3)δ173.61,165.93,144.81,131.59,129.81,108.75,92.40,42.19,40.54,36.86,
36.07；HRMS Calcd for C12H13IN2O2[M+H]+:345.0022,Found:345.0008.
Embodiment 15：The synthesis of 4- methyl-N- dimethylacetamide base indol-2-ones
Weigh 2- methyl-N- dimethylacetamide base phenyl acetamide 1o (0.0468g, 0.2mmol), palladium (0.0022g,
0.01mmol) it is dissolved in 1mL toluene, adds PhI (OAc)2(0.0966g, 0.3mmol).Mixture is heated to 60 DEG C, TLC with
Track reaction is fully completed until reaction.Reaction terminates rear crude on silica gel column chromatography for separation (petroleum ether:Ethyl acetate=1:2)
Compound 2o is obtained after purification.It is 82% to separate yield.
2o:1H NMR(400MHz,CDCl3) δ 7.16-7.12 (m, 1H), 6.85 (d, J=8.00Hz, 1H), 6.64 (d, J
=7.60Hz, 1H), 4.50 (s, 2H), 3.48 (s, 2H), 3.10 (s, 3H), 2.96 (s, 3H), 2.26 (s, 3H)；13C NMR
(101MHz,CDCl3)δ175.39,166.31,144.31,134.18,128.07,123.99,123.10,106.57,42.13,
36.80,36.00,34.79,18.72；HRMS Calcd for C13H16N2O2[M+H]+:233.1290,Found:
233.1277.
Embodiment 16：The synthesis of 4,6- dimethyl-N-dimethylacetamide base indol-2-ones
Weigh 2,4- dimethyl-N-dimethylacetamide base phenyl acetamide 1p (0.0496g, 0.2mmol), palladium
(0.0022g, 0.01mmol) is dissolved in 1mL toluene, adds PhI (OAc)2(0.0966g, 0.3mmol).Mixture is heated to 60
DEG C, TLC tracking reaction is fully completed until reaction.Reaction terminates rear crude on silica gel column chromatography for separation (petroleum ether:Acetic acid second
Ester=1:2) compound 2p is obtained after purifying.It is 62% to separate yield.
2p:1H NMR(400MHz,CDCl3)δ6.67(s,1H),6.47(s,1H),4.48(s,2H),3.43(s,2H),
3.11(s,3H),2.97(s,3H),2.30(s,3H),2.21(s,3H)；13C NMR(101MHz,CDCl3)δ175.78,
166.38,144.37,138.06,133.82,124.65,120.10,107.38,42.10,36.78,36.01,34.56,
21.88,18.64；HRMS Calcd for C14H18N2O2[M+H]+:247.1447,Found:247.1443.
Embodiment 17：The synthesis of 4,6- bis- chloro- N- dimethylacetamides base indol-2-ones
Weigh the chloro- N- dimethylacetamides base phenyl acetamide 1q (0.0576g, 0.2mmol) of 2,4- bis-, palladium
(0.0022g, 0.01mmol) is dissolved in 1mL toluene, adds PhI (OAc)2(0.0966g, 0.3mmol).Mixture is heated to 60
DEG C, TLC tracking reaction is fully completed until reaction.Reaction terminates rear crude on silica gel column chromatography for separation (petroleum ether:Acetic acid second
Ester=1:2) compound 2q is obtained after purifying.It is 47% to separate yield.
2q:1H NMR(400MHz,CDCl3)δ7.03(s,1H),6.68(s,1H),4.47(s,2H),3.56(s,2H),
3.12(s,3H),2.98(s,3H)；13C NMR(101MHz,CDCl3)δ174.28,165.44,146.46,134.73,
130.98,122.57,121.49,108.38,42.02,36.75,36.09,34.99；HRMS Calcd for
C12H12Cl2N2O2[M+H+]:287.0354,Found:287.0229.
Embodiment 18：The synthesis of 5,6- dimethoxy-N- dimethylacetamide base indol-2-ones
Weigh 3,4- dimethoxy-N- dimethylacetamide base phenyl acetamide 1s (0.0560g, 0.2mmol), palladium
(0.0022g, 0.01mmol) is dissolved in 1mL toluene, adds PhI (OAc)2(0.0966g, 0.3mmol).Mixture is heated to 60
DEG C, TLC tracking reaction is fully completed until reaction.Reaction terminates rear crude on silica gel column chromatography for separation (petroleum ether:Acetic acid second
Ester=1:2) compound 2s is obtained after purifying.It is 51% to separate yield.
2s:1H NMR(400MHz,CDCl3)δ6.87(s,1H),6.57(s,1H),4.50(s,2H),3.89(s,3H),
3.84(s,3H),3.54(s,2H),3.12(s,3H),2.97(s,3H)；13C NMR(101MHz,CDCl3)δ175.70,
166.68,149.65,145.41,138.45,115.10,109.92,95.70,57.15,56.68,42.57,37.11,
36.10,35.93；HRMS Calcd for C14H18Cl2N2O4[M+H+]:279.1345,Found:279.1300.
Embodiment 19：The synthesis of 5,6- bis- chloro- N- dimethylacetamides base indol-2-ones
Weigh the chloro- N- dimethylacetamides base phenyl acetamide 1t (0.0576g, 0.2mmol) of 3,4- bis-, palladium
(0.0022g, 0.01mmol) is dissolved in 1mL toluene, adds PhI (OAc)2(0.0966g, 0.3mmol).Mixture is heated to 60
DEG C, TLC tracking reaction is fully completed until reaction.Reaction terminates rear crude on silica gel column chromatography for separation (petroleum ether:Acetic acid second
Ester=1:2) compound 2t is obtained after purifying.It is 52% to separate yield.
2t:1H NMR(400MHz,CDCl3)δ7.31(s,1H),6.86(s,1H),4.48(s,2H),3.57(s,2H),
3.12(s,3H),2.98(s,3H)；13C NMR(101MHz,CDCl3)δ174.71,165.49,144.33,132.04,
126.37,124.31,111.05,41.90,36.76,36.09,35.29；HRMS Calcd for C12H12Cl2N2O2[M+H+]:
287.0354,Found:287.0330.
Embodiment 20：The synthesis of 3- methyl -6- isobutyl group-N- dimethylacetamide base indol-2-ones
Weigh 4- isobutyl groups-Alpha-Methyl-N- dimethylacetamide base phenyl acetamide 1u (0.0580g, 0.2mmol), palladium
(0.0022g, 0.01mmol) is dissolved in 1mL toluene, adds PhI (OAc)2(0.0966g, 0.3mmol).Mixture is heated to 60
DEG C, TLC tracking reaction is fully completed until reaction.Reaction terminates rear crude on silica gel column chromatography for separation (petroleum ether:Acetic acid second
Ester=1:2) compound 2u is obtained after purifying.It is 91% to separate yield.
2u:1H NMR(400MHz,CDCl3) δ 7.12 (d, J=7.60Hz, 1H), 6.82 (d, J=7.60Hz, 1H), 6.62
(s, 1H), 4.55-4.43 (m, 2H), 3.10 (s, 3H), 2.96 (s, 3H), 2.45 (d, J=7.20Hz, 2H), 1.88-1.81
(m, 1H), 1.48 (d, J=7.60Hz, 3H), 0.89 (d, J=6.80Hz, 6H)；13C NMR(101MHz,CDCl3)δ179.26,
166.45,143.29,142.05,127.87,123.50,123.22,109.72,45.85,42.18,40.41,36.87,
36.01,30.44,22.59,22.57,15.80；HRMS Calcd for C17H24N2O2[M+H+]:289.1916.；Found:
289.1905.
Embodiment 21：The synthesis of 3,3- dimethyl-N-dimethylacetamide base indol-2-ones
Weigh α, alpha-alpha-dimethyl-N- dimethylacetamide base phenyl acetamide 1v (0.0496g, 0.2mmol), palladium
(0.0022g, 0.01mmol) is dissolved in 1mL toluene, adds PhI (OAc)2(0.0966g, 0.3mmol).Mixture is heated to 60
DEG C, TLC tracking reaction is fully completed until reaction.Reaction terminates rear crude on silica gel column chromatography for separation (petroleum ether:Acetic acid second
Ester=1:2) compound 2v is obtained after purifying.It is 92% to separate yield.
2v:1H NMR(400MHz,CDCl3) δ 7.22-7.19 (m, 2H), 7.06-7.03 (m, 1H), 6.83 (d, J=
7.60Hz,1H),4.51(s,2H),3.09(s,3H),2.96(s,3H),1.41(s,6H)；13C NMR(101MHz,CDCl3)δ
181.62,166.37,142.05,135.64,127.86,122.81,122.43,108.95,44.34,41.98,36.75,
35.98,24.65；HRMS Calcd for C14H18N2O2[M+H+]:247.1447,Found:247.1434.
Embodiment 22：The synthesis of the chloro- N- dimethylacetamides base indol-2-ones of 3- acetoxyl groups -4-
Weigh the chloro- α of 2--acetoxyl group-N- dimethylacetamide base phenyl acetamide 1w (0.0624g, 0.2mmol), palladium
(0.0022g, 0.01mmol) is dissolved in 1mL toluene, adds PhI (OAc)2(0.0966g, 0.3mmol).Mixture is heated to 60
DEG C, TLC tracking reaction is fully completed until reaction.Reaction terminates rear crude on silica gel column chromatography for separation (petroleum ether:Acetic acid second
Ester=1:2) compound 2w is obtained after purifying.It is 84% to separate yield.
2w:1H NMR(400MHz,CDCl3) δ 7.27-7.23 (m, 1H), 7.02 (d, J=8.40Hz, 1H), 6.76 (d, J
=8.00Hz, 1H), 6.18 (s, 1H), 4.66 (d, J=16.40Hz, 1H), 4.34 (d, J=16.40Hz, 1H), 3.11 (s,
3H),2.98(s,3H),2.20(s,3H)；13C NMR(101MHz,CDCl3)δ171.77,169.67,165.66,145.57,
131.68,131.66,121.64,108.22,69.00,42.48,36.91,36.09,20.52；HRMS Calcd for
C14H15ClN2O2[M+H+]:311.0799,Found:311.0790.
Embodiment 23：The synthesis of α-acetoxyl group-N- dimethylacetamide base indol-2-ones
Weigh α-acetoxyl group-N- dimethylacetamide base phenyl acetamide 1x (0.0556g, 0.2mmol), palladium
(0.0022g, 0.01mmol) is dissolved in 1mL toluene, adds PhI (OAc)2(0.0966g, 0.3mmol).Mixture is heated to 60
DEG C, TLC tracking reaction is fully completed until reaction.Reaction terminates rear crude on silica gel column chromatography for separation (petroleum ether:Acetic acid second
Ester=1:2) compound 2x is obtained after purifying.It is 91% to separate yield.
2x:1H NMR(400MHz,CDCl3) δ 7.35 (d, J=7.20Hz, 1H), 7.32-7.28 (m, 1H), 7.07-7.03
(m, 1H), 6.84 (d, J=7.60Hz, 1H), 6.05 (s, 1H), 4.63 (d, J=8.00Hz, 1H), 4.39 (d, J=8.00Hz,
1H),3.11(s,3H),2.98(s,3H),2.19(s,3H)；13C NMR(101MHz,CDCl3)δ172.55,170.52,
165.85,144.01,130.56,125.83,124.37,123.47,109.64,70.04,42.27,36.90,36.08,
20.95；HRMS Calcd for C14H16N2O4[M+H+]:277.1188,Found:277.1182.
Embodiment 24：2- (6 '-chloro- 2 ' oxo spiral shell [indoline of ring butyl- 1,3 '] -1- bases)-N, N dimethyl acetamide
Synthesis
Weigh 1- (4- chlorphenyls)-N- dimethylacetamide tetramethylcyclobutyl formamide 1y (0.0520g, 0.2mmol), palladium
(0.0022g, 0.01mmol) is dissolved in 1mL toluene, adds PhI (OAc)2(0.0966g, 0.3mmol).Mixture is heated to 60
DEG C, TLC tracking reaction is fully completed until reaction.Reaction terminates rear crude on silica gel column chromatography for separation (petroleum ether:Acetic acid second
Ester=1:2) compound 2y is obtained after purifying.It is 92% to separate yield.
2y:1H NMR(400MHz,CDCl3) δ 7.38 (d, J=8.00Hz, 1H), 7.02 (d, J=7.60Hz, 1H), 6.73
(s,1H),4.43(s,2H),3.08(s,3H),2.94(s,3H),2.68–2.58(m,2H),2.38–2.27(m,3H),2.26–
2.13(m,1H)；13C NMR(101MHz,CDCl3)δ180.42,165.88,143.58,133.53,132.46,109.30,
47.86,41.80,36.67,35.94,31.57,16.81；HRMS Calcd for C14H15ClN2O2[M+H+]:293.1057,
Found:293.1047.
Embodiment 25：The synthesis of N, N- dimethyl -2- (6- methyl -2--oxindole quinoline -1- bases) propionamide
Weigh N, N- dimethyl -2- (2- (p-methylphenyl) acetamido) propionamide 1z (0.0496g, 0.2mmol), acetic acid
Palladium (0.0022g, 0.01mmol) is dissolved in 1mL toluene, adds PhI (OAc)2(0.0966g, 0.3mmol).Mixture is heated to
60 DEG C, TLC tracking reaction is fully completed until reaction.Reaction terminates rear crude on silica gel column chromatography for separation (petroleum ether:Acetic acid
Ethyl ester=1:2) compound 2z is obtained after purifying.It is 72% to separate yield.
2z:1H NMR(400MHz,CDCl3) δ 7.12 (d, J=7.60Hz, 1H), 7.01 (s, 1H), 6.85 (d, J=
7.20Hz, 1H), 5.42 (q, J=6.80Hz, 1H), 3.51 (s, 2H), 2.94 (s, 3H), 2.90 (s, 3H), 2.34 (s, 3H),
1.51 (d, J=6.80Hz, 3H)；13C NMR(101MHz,CDCl3)δ174.62,169.39,142.79,138.55,124.29,
123.35,121.46,111.85,47.10,37.21,36.52,35.20,22.10,14.85；HRMS Calcd for
C14H18N2O2[M+H+]:247.1447,Found:247.1444.
Embodiment 26：The synthesis of N, N- dimethyl -2- (6- methyl -2--oxindole quinoline -1- bases) butyramide
Weigh N, N- dimethyl -2- (2- (p-methylphenyl) acetamido) butyramide 1 I (0.0524g, 0.2mmol), acetic acid
Palladium (0.0022g, 0.01mmol) is dissolved in 1mL toluene, adds PhI (OAc)2(0.0966g, 0.3mmol).Mixture is heated to
60 DEG C, TLC tracking reaction is fully completed until reaction.Reaction terminates rear crude on silica gel column chromatography for separation (petroleum ether:Acetic acid
Ethyl ester=1:2) compound 2 I is obtained after purifying.It is 70% to separate yield.
2Ⅰ:1H NMR(400MHz,CDCl3) δ 7.11 (d, J=7.60Hz, 1H), 7.08 (s, 1H), 6.84 (d, J=
7.60Hz,1H),5.23–5.19(m,1H),3.60–3.46(m,2H),2.95(s,3H),2.93(s,3H),2.33(s,3H),
2.16-1.98 (m, 2H), 0.87 (t, J=7.40Hz, 3H)；13C NMR(101MHz,CDCl3)δ175.26,169.00,
142.97,138.47,124.17,123.33,121.31,112.30,52.93,37.24,36.40,35.09,22.10,
22.03,10.61；HRMS Calcd for C15H20N2O2[M+H+]:261.1603,Found:261.1599.
Embodiment 27：The synthesis of N, N, 3- trimethyl -2- (6- methyl -2--oxindole quinoline -1- bases) butyramide
Weigh N, N, 3- trimethyls -2- (2- (p-methylphenyl) acetamido) butyramide 1 II (0.0552g, 0.2mmol),
Palladium (0.0022g, 0.01mmol) is dissolved in 1mL toluene, adds PhI (OAc)2(0.0966g, 0.3mmol).Mixture adds
To 60 DEG C, TLC tracking reaction is fully completed heat until reaction.Reaction terminates rear crude on silica gel column chromatography for separation (petroleum ether:
Ethyl acetate=1:2) compound 2 II is obtained after purifying.It is 70% to separate yield.
2Ⅱ:1H NMR(400MHz,CDCl3) δ 7.33 (s, 1H), 7.10 (d, J=7.60Hz, 1H), 6.84 (d, J=
7.60Hz, 1H), 4.94 (d, J=10.80Hz, 1H), 3.04 (s, 3H), 2.94 (s, 3H), 2.91-2.82 (m, 1H), 2.34
(s, 3H), 1.05 (d, J=6.40Hz, 3H), 0.75 (d, J=6.80Hz, 3H)；13C NMR(101MHz,CDCl3)δ175.59,
168.38,143.36,138.42,124.01,123.34,121.10,113.17,57.36,37.50,36.31,35.09,
26.84,22.16,20.55,18.44；HRMS Calcd for C16H22N2O2[M+H+]:275.1760,Found:
275.1444.
Embodiment 28：The synthesis of N, N, 4- trimethyl -2- (6- methyl -2--oxindole quinoline -1- bases) pentanamide
Weigh N, N, 4- trimethyls -2- (2- (p-methylphenyl) acetamido) pentanamide 1 III (0.0580g, 0.2mmol),
Palladium (0.0022g, 0.01mmol) is dissolved in 1mL toluene, adds PhI (OAc)2(0.0966g, 0.3mmol).Mixture adds
To 60 DEG C, TLC tracking reaction is fully completed heat until reaction.Reaction terminates rear crude on silica gel column chromatography for separation (petroleum ether:
Ethyl acetate=1:2) compound 2 III is obtained after purifying.It is 55% to separate yield.
2Ⅲ:1H NMR(400MHz,CDCl3) δ 7.11 (d, J=4.80Hz, 1H), 7.10 (s, 1H), 6.84 (d, J=
7.60Hz, 1H), 5.39 (t, J=7.40Hz, 1H), 3.51 (q, J=16.90Hz, 2H), 2.97 (s, 3H), 2.93 (s, 3H),
1.95 (t, J=7.00Hz, 2H), 1.49-1.41 (m, 1H), 0.98 (d, J=6.80Hz, 3H), 0.89 (d, J=6.80Hz,
3H)；13C NMR(101MHz,CDCl3)δ175.02,169.25,143.10,138.45,124.15,123.28,121.41,
112.45,49.68,37.67,37.34,36.50,35.15,24.87,23.35,22.43,22.14；HRMS Calcd for
C17H24N2O2[M+H+]:289.1916,Found:289.1911.
Embodiment 29：The synthesis of N, N, 3- trimethyl -2- (6- methyl -2--oxindole quinoline -1- bases) pentanamide
Weigh N, N, 3- trimethyls -2- (2- (p-methylphenyl) acetamido) pentanamide 1 IV (0.0580g, 0.2mmol),
Palladium (0.0022g, 0.01mmol) is dissolved in 1mL toluene, adds PhI (OAc)2(0.0966g, 0.3mmol).Mixture adds
To 60 DEG C, TLC tracking reaction is fully completed heat until reaction.Reaction terminates rear crude on silica gel column chromatography for separation (petroleum ether:
Ethyl acetate=1:2) compound 2 IV is obtained after purifying.It is 54% to separate yield.
2Ⅳ:1H NMR(400MHz,CDCl3) δ 7.35 (s, 1H), 7.08 (d, J=7.60Hz, 1H), 6.83 (d, J=
7.60Hz, 1H), 5.03 (d, J=10.80Hz, 1H), 3.59-3.43 (m, 2H), 3.06 (s, 3H), 2.93 (s, 3H), 2.70-
2.61 (m, 1H), 2.34 (s, 3H), 1.21-1.14 (m, 1H), 1.03-0.92 (m, 1H), 0.98 (d, J=6.40Hz, 3H),
0.79 (t, J=7.40Hz, 3H)；13C NMR(101MHz,CDCl3)δ175.56,168.48,143.43,138.35,123.93,
123.28,121.08,113.31,56.18,37.56,36.30,35.09,32.56,24.35,22.13,16.51,10.92；
HRMS Calcd for C17H24N2O2[M+H+]:289.1916,Found:289.1905.
Embodiment 30：2- cyclohexyl-N, N,-dimethyl -2- (6- methyl -2--oxindole quinoline -1- bases) acetamide
Synthesis
Weigh 2- cyclohexyl-N, N,-dimethyl -2- (2- (p-methylphenyl) acetamido) acetamide 1 V (0.0632g,
0.2mmol), palladium (0.0022g, 0.01mmol) is dissolved in 1mL toluene, adds PhI (OAc)2(0.0966g,
0.3mmol).Mixture is heated to 60 DEG C, and TLC tracking reaction is fully completed until reaction.Reaction terminates rear crude on silica gel
Column chromatography for separation (petroleum ether:Ethyl acetate=1:2) compound 2 V is obtained after purifying.It is 48% to separate yield.
2Ⅴ:1H NMR(400MHz,CDCl3) δ 7.32 (s, 1H), 7.07 (d, J=7.60Hz, 1H), 6.81 (d, J=
7.60Hz, 1H), 5.01 (d, J=10.80Hz, 1H), 3.57-3.41 (m, 2H), 3.01 (s, 3H), 2.90 (s, 3H), 2.57-
2.49 (m, 1H), 2.33 (s, 3H), 1.91 (d, J=12.00Hz, 1H), 1.69 (d, J=12.00Hz, 1H), 1.61 (s, 2H),
1.34-1.24 (m, 2H), 1.11 (t, J=9.40Hz, 2H), 0.98-0.86 (m, 2H)；13C NMR(101MHz,CDCl3)δ
175.49,168.20,143.39,138.29,123.87,123.21,120.97,113.03,56.01,37.39,36.17,
35.48,34.95,31.09,28.13,26.40,25.77,25.72,22.07；HRMS Calcd for C19H26N2O2[M+H+]:315.2073,Found:315.2066.
In a word, the invention discloses a kind of preparation method of indol-2-one derivates, to substitute 2- phenylacetyl amido acetyl
Dimethylamine derivative is substrate, using palladium salts such as palladiums as catalyst, in the organic solvents such as toluene, is existed with iodobenzene diacetate
25-80 DEG C of reaction, obtained multiple indol-2-one derivates derivatives that can be in high yield.
Described above is only the preferred embodiment of the present invention, is not intended to limit the invention, it is noted that for this skill
For the those of ordinary skill in art field, without departing from the technical principles of the invention, can also make it is some improvement and
Modification, these improvement and modification also should be regarded as protection scope of the present invention.
Claims (8)
1. a kind of preparation method of N- dimethylacetamides base indol-2-one derivates, it is characterised in that comprise the following steps：
By the substitution N- dimethylacetamide base phenyl acetamide derivatives of formula (1) and iodobenzene diacetate palladium salt catalyst effect
Under, reacted in organic solvent at 25-80 DEG C, obtain the N- dimethylacetamide base indol-2-one derivates of formula (2)：
Wherein, R1、R2、R3、R4、R5、R6Independently selected from hydrogen, alkyl, alkoxy, phenyl, acetoxyl group, halogen, aromatic radical or
Trifluoromethyl.
2. the preparation method of N- dimethylacetamides base indol-2-one derivates according to claim 1, it is characterised in that：
R1、R2、R3、R4、R5、R6It is hydrogen；
Or R1、R2、R3、R4One of which be alkyl, alkoxy, aromatic radical, halogen or trifluoromethyl, other threes are hydrogen,
R5、R6It is hydrogen；
Or R1、R2、R4、R5It is hydrogen, R3For alkyl or aromatic radical, R6For C1-C6Alkyl；
Or R4、R6It is hydrogen, R5For alkyl or acetoxyl group, R1、R2Or R3In one of which be alkyl, aromatic radical or halogen,
Other are both at hydrogen.
3. the preparation method of N- dimethylacetamides base indol-2-one derivates according to claim 1, it is characterised in that：
The alkyl is C1-C6Alkyl.
4. the preparation method of N- dimethylacetamides base indol-2-one derivates according to claim 1, it is characterised in that：
The alkoxy is C1-C6Alkoxy.
5. the preparation method of N- dimethylacetamides base indol-2-one derivates according to claim 1, it is characterised in that：
The aromatic radical is phenyl.
6. the preparation method of N- dimethylacetamides base indol-2-one derivates according to claim 1, it is characterised in that：
The palladium salt catalyst is palladium or palladium bichloride.
7. the preparation method of N- dimethylacetamides base indol-2-one derivates according to claim 1, it is characterised in that：
The organic solvent is toluene, 1,2- dichloroethanes, tetrahydrofuran, 1,4- dioxane or acetic anhydride.
8. the preparation method of N- dimethylacetamides base indol-2-one derivates according to claim 1, it is characterised in that：
The mol ratio of the substitution N- dimethylacetamide bases phenyl acetamide derivative, iodobenzene diacetate and palladium salt catalyst is 1:1-2:
0.05-0.1。
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|---|---|---|---|---|
| CN113214134A (en) * | 2021-04-30 | 2021-08-06 | 南通大学 | Synthesis method of quaternary carbon oxoindole skeleton |
| US11365210B2 (en) | 2014-02-24 | 2022-06-21 | Ventana Medical Systems, Inc. | Quinone methide analog signal amplification |
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US11365210B2 (en) | 2014-02-24 | 2022-06-21 | Ventana Medical Systems, Inc. | Quinone methide analog signal amplification |
| US11780863B2 (en) * | 2014-02-24 | 2023-10-10 | Ventana Medical Systems, Inc. | Quinone methide analog signal amplification |
| CN113214134A (en) * | 2021-04-30 | 2021-08-06 | 南通大学 | Synthesis method of quaternary carbon oxoindole skeleton |
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