CN107056635B - A kind of synthetic method of alkynyl amide class compound - Google Patents
A kind of synthetic method of alkynyl amide class compound Download PDFInfo
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Abstract
The invention discloses a kind of synthetic methods of alkynyl amide class compound, by acetylene compound (0.1 mmol), benzyl isonitrile (0.25 mmol), organic acid sodium (0.3 mmol), H2O(0.1 mmol) and palladium catalyst (0.01 mmol) be mixed in 15 mL tube sealings, be added 2.0 mL solvents, 60oIt is stirred 2 hours under C；It whether complete reacts with TLC tracking, is filtered after having reacted by decompression and remove solvent, residue purifies through Flash silica column analysis layer and (ethyl acetate/petroleum ether=1: 25) obtains alkynyl amide compound.The present invention synthesizes the new method of alkynyl amide compound, and sharpest edges are to overcome the disadvantage of alkynes sodium, the stringent preparation of alkynes Grignard Reagent and reaction condition more harshness.Using acetylene compound simple and easy to get, benzyl isonitrile and organic acid sodium as raw material, raw material is easy to get synthetic method of the present invention, easy to operate, waits until that outstanding yield obtains alkynyl amide class compound, is with a wide range of applications under more mild experiment condition.
Description
Technical field
It is specifically a kind of with acetylene compound, benzyl isonitrile and organic acid the present invention relates to the synthesis of alkynyl amide class compound
Sodium is the method for Material synthesis alkynyl amide class compound.
Background technique
Ynylamide derivative is important the element in organic synthesis, and this kind of compound is in natural products
It plays a crucial role, is the key intermediate in heterocyclic synthesis.
3- benzo-aza skeleton is widely present in native compound and important drug, their challenging chemistry
Structure and interesting bioactivity.It is effective that the various substitutions of 3- benzo-aza structure have also been studied for synthesis
Nmda receptor antagonist.Most commonly the medium sized ring of 3- benzo-aza skeleton be constructed by intramolecular realization, and
Alkynyl amide exactly constructs the common intermediate of 3- benzo-aza skeleton.The 3- benzo nitrogen compound constructed by alkynyl amide compound is
It is studied extensively for treating neurodegenerative disease such as Hun-tington's, A Erci Mo's disease and amyotrophic lateral are hard
Change (Org. Lett.,2007,9,3017-3020).Replace alkynyl amide as raw material using adjacent halogenated aromatic base, synthesis is in medicine, change
The fields such as work have the 2- amino indole cycle compound (Yao Peiyuan, University Of Tianjin Ph.D. Dissertation) of important use.Metal is urged
Change chromone class and isocoumarin class compound (Liu that alkynyl amide preparation has the important function such as antibacterial, anticancer, biological enzyme inhibitor
Hong Xu, Zhengzhou University's master thesis).
It is most of to use alkynes sodium, alkynes Grignard Reagent and amino in the synthetic method for preparing alkynyl amide class compound in the past
Formic acid halogen (Cl, Br) reaction.However, the preparation condition of alkynes sodium, alkynes Grignard Reagent is more harsh, its synthesis is influenced.
Summary of the invention
The purpose of the present invention is using acetylene compound, benzyl isonitrile and organic acid sodium as raw material, in the effect of palladium salt catalyst
Under synthesized alkynyl amide class compound.This method raw material is easy to get, easy to operate, and reaction condition is mild, before having good application
Scape.
Realizing the technical solution of the object of the invention is:
A kind of synthetic method of alkynyl amide class compound, synthetic method general formula are as follows:
Wherein, R1=aryl, cyclopropyl；
R2=benzyl
R3=alkyl, aryl；
Catalyst are as follows: Pd (dppf) Cl2、Pd(OAc)2；
Solvent are as follows: acetonitrile, DMF.
The universal synthesis method of the alkynyl amide class compound is:
By acetylene compound (0.1 mmol), benzyl isonitrile (0.25 mmol), organic acid sodium (0.3 mmol), H2O(0.1
Mmol it) is mixed in 15 mL tube sealings with palladium catalyst (0.01 mmol), 2.0 mL solvents is added, 60oStirring 2 is small under C
When；It is whether complete with TLC tracking reaction, it is filtered after having reacted by decompression and removes solvent, residue is analysed through Flash silica column
Layer purifying (ethyl acetate/petroleum ether=1:25) obtains alkynyl amide compound.
The structural formula of the alkynyl amide class compound of synthesis is as follows:
In order to verify the source of oxygen in the reaction product We conducted following experiment (experiment using phenylacetylene, benzyl isonitrile,
Sodium acetate is reaction substrate):
(1) argon gas protection it is lower toward addition phenylacetylene in dry flask (0.1 mmol, 0.0102 g), benzyl isonitrile (0.25
Mmol, 0.0293 g), (0.3 mmol, 0.0246 g) and Pd (dppf) Cl for sodium acetate2(0.01 mmol, 0.0018 g), with
2.0 mL are super, and dry acetonitrile makees solvent, 60oIt is stirred 2 hours under C, is not found product 4a generation.
(2) be added in the lower dry flask of oxygen protection phenylacetylene (0.1 mmol, 0.0102 g), benzyl isonitrile (0.25
Mmol, 0.0293 g), (0.3 mmol, 0.0246 g) and Pd (dppf) Cl for sodium acetate2(0.01 mmol, 0.0018 g), with
2.0 mL are super, and dry acetonitrile makees solvent, 60oIt is stirred 2 hours under C, is not found product 4a generation.
(3) the lower addition phenylacetylene into flask of argon gas protection (0.1 mmol, 0.0102 g), benzyl isonitrile (0.25 mmol,
0.0293 g), sodium acetate (0.3 mmol, 0.0246 g), H2O(0.1 mmol, 0.0018 g) and Pd (dppf) Cl2(0.01
Mmol, 0.0018 g), makees solvent with the super dry acetonitrile of 2.0 mL, 60oIt is stirred 2 hours under C, discovery has product 4a generation,
Structural formula isYield: 85%.
By reacting above it can be concluded that under anhydrous and oxygen-free and anhydrous aerobic conditions, produced without target
The generation of object 4a；In the case where there is water oxygen free condition, there is the generation of target product 4a, this illustrates that the oxygen in the reaction product alkynyl amide comes
Oxygen in water.
The present invention synthesize alkynyl amide compound new method, sharpest edges be overcome alkynes sodium, alkynes Grignard Reagent it is stringent
The disadvantage of preparation and reaction condition more harshness.Synthetic method of the present invention with acetylene compound simple and easy to get, benzyl isonitrile and
Organic acid sodium is raw material, and raw material is easy to get, easy to operate, until outstanding yield obtains under more mild experiment condition
Alkynyl amide class compound, is with a wide range of applications.
Specific embodiment
Below with reference to the synthetic method and Characterization of The Products of a kind of in embodiment ten alkynyl amide class compounds to the content of present invention
It is further described, but is not limitation of the invention.
Embodiment 1
The synthesis of N- acetyl group-N- benzyl -3- phenyl propyne amide:
By phenylacetylene (0. 1 mmol, 0.0102 g), benzyl isonitrile (0.25 mmol, 0.0293 g), sodium acetate (0.3
Mmol, 0.0246 g), H2O(0.1 mmol, 0.0018 g) and Pd (dppf) Cl2(0.01 mmol, 0.0018 g) is mixed in 15
In mL tube sealing, 2.0 mL acetonitrile as solvents are added, 60oIt is stirred 2 hours under C；It is whether complete with TLC tracking reaction, wait react
It is filtered after complete by decompression and removes solvent, residue is obtained through Flash silica column analysis layer purifying (ethyl acetate/petroleum ether=1:25)
8.68 mg of alkynyl amide compound (yellow oily) 4a, yield 85%；
Characterization of The Products1H NMR (400 MHz, CDCl3) δ 7.50 – 7.44 (m, 3H), 7.38 (d, J =
7.2 Hz, 2H), 7.34 (dd, J = 5.8, 2.1 Hz, 4H), 7.30 – 7.26 (m, 1H), 5.25 (s,
2H), 2.64 (s, 3H) ppm;13C NMR (100 MHz, CDCl3) δ 172.53, 155.72, 136.98,
132.70, 130.99, 128.66, 128.56, 127.49, 127.26, 119.34, 94.07, 82.67, 48.62,
27.62 ppm;HRMS (m/z) (APCI): calcd for C18H16NO2278.11756 [M+H+]; found
278.11689。
Embodiment 2
N- acetyl group-N- benzyl -3-(4- aminomethyl phenyl) propine amide synthesis:
Will to methyl phenylacetylene (0. 1 mmol, 0.0116 g), benzyl isonitrile (0.25 mmol, 0.0293 g), sodium acetate
(0.3 mmol, 0.0246 g), H2O(0.1 mmol, 0.0018 g) and Pd (dppf) Cl2(0.01 mmol, 0.0018 g) mixes
Make solvent together in 2.0 mL DMF in 15 mL tube sealings, are added, 60oIt is stirred 2 hours under C；It is whether complete with TLC tracking reaction
Entirely, after having reacted by decompression filter remove solvent, residue through Flash silica column analysis layer purifying (ethyl acetate/petroleum ether=
1:25) obtain 9.98 mg of alkynyl amide compound (yellow solid) 4b, yield 86%；
Characterization of The Products1H NMR (400 MHz, CDCl3) δ 7.35 (dd, J = 9.3, 2.8 Hz, 3H), 7.34
– 7.31 (m, 4H), 7.30 – 7.25 (m, 2H), 7.16 (d, J = 7.9 Hz, 2H), 5.22 (s, 2H),
2.61 (s, 3H), 2.36 (s, 3H) ppm;13C NMR (100 MHz, CDCl3) δ 172.63, 155.91,
141.88, 137.15, 132.80, 129.54, 128.72, 128.62, 128.53, 127.87, 127.52,
127.36, 116.32, 94.81, 82.58, 48.69, 27.63, 21.79 ppm; HRMS (m/z) (APCI):
calcd for C19H18NO2292.13321 [M+H+]; found 292.13342。
Embodiment 3
N- acetyl group-N- benzyl -3-(3- aminomethyl phenyl) propine amide synthesis:
Will between methyl phenylacetylene (0. 1 mmol, 0.0116 g), benzyl isonitrile (0.25 mmol, 0.0293 g), sodium acetate
(0.3 mmol, 0.0246 g), H2O(0.1 mmol, 0.0018 g) and Pd (OAc)2 (0.01 mmol, 0.0024 g) mixes
In 15 mL tube sealings, 2.0 mL acetonitrile as solvents are added, 60oIt is stirred 2 hours under C；It is whether complete with TLC tracking reaction,
After having reacted by decompression filter remove solvent, residue through Flash silica column analysis layer purifying (ethyl acetate/petroleum ether=1:
25) 9.86 mg of alkynyl amide compound (yellow solid) 4c, yield 85% are obtained；
Characterization of The Products1H NMR (400 MHz, CDCl3) δ 7.32 (d, J = 6.8 Hz, 4H), 7.23 (t, J
= 5.0 Hz, 5H), 5.22 (s, 2H), 2.61 (s, 3H), 2.30 (s, 3H) ppm;13C NMR (100 MHz,
CDCl3) δ 172.39, 155.63, 138.42, 136.98, 133.09, 131.84, 129.73, 128.46,
128.41, 127.36, 127.20, 119.06, 94.33, 82.40, 48.50, 27.47, 21.01 ppm; HRMS
(m/z) (APCI): calcd for C19H18NO2292.13321 [M+H+]; found 292.13293。
Embodiment 4
N- acetyl group-N- benzyl -3-(4- tert-butyl-phenyl) propine amide synthesis:
Will to tert-butyl benzene acetylene (0. 1 mmol, 0.0158 g), benzyl isonitrile (0.25 mmol, 0.0293 g), acetic acid
Sodium (0.3 mmol, 0.0246 g), H2O(0.1 mmol, 0.0018 g) and Pd (dppf) Cl2(0.01 mmol, 0.0018 g)
It is mixed in 15 mL tube sealings, 2.0 mL DMF is added and make solvent, 60oIt is stirred 2 hours under C；It is whether complete with TLC tracking reaction
Entirely, after having reacted by decompression filter remove solvent, residue through Flash silica column analysis layer purifying (ethyl acetate/petroleum ether=
1:25) obtain alkynyl amide compound (yellow oily) 4d14.06 mg, yield 89%；
Characterization of The Products1H NMR (400 MHz, CDCl3) δ 7.40 (dd, J = 9.8, 3.3 Hz, 4H), 7.32
(d, J = 6.6 Hz, 4H), 7.25 (dd, J = 7.9, 4.8 Hz, 1H), 5.22 (s, 2H), 2.61 (s,
3H), 1.29 (s, 9H) ppm;13C NMR (100 MHz, CDCl3) δ 172.51, 155.83, 154.79,
137.06, 132.60, 128.52, 127.42, 127.27, 125.72, 116.25, 94.64, 82.44, 48.59,
35.04, 30.94, 27.54 ppm; HRMS (m/z) (APCI): calcd for C22H24NO2334.18016 [M+H+]; found 334.18112。
Embodiment 5
N- acetyl group-N- benzyl -3-(4- methoxyphenyl) propine amide synthesis:
Will to Methoxy-phenylacetylene (0. 1 mmol, 0.0132 g), benzyl isonitrile (0.25 mmol, 0.0293 g), acetic acid
Sodium (0.3 mmol, 0.0246 g), H2O(0.1 mmol, 0.0018 g) and Pd (OAc)2 (0.01 mmol, 0.0024 g) mixes
Together in 15 mL tube sealings, 2.0 mL acetonitrile as solvents are added, 60oIt is stirred 2 hours under C；It is whether complete with TLC tracking reaction
Entirely, after having reacted by decompression filter remove solvent, residue through Flash silica column analysis layer purifying (ethyl acetate/petroleum ether=
1:25) obtain alkynyl amide compound (yellow solid) 4e11.35 mg, yield 86%；
Characterization of The Products1H NMR (400 MHz, CDCl3) δ 7.40 (d, J = 8.7 Hz, 2H), 7.34 –
7.29 (m, 4H), 7.26 (d, J = 3.0 Hz, 1H), 5.22 (s, 2H), 3.81 (s, 3H), 2.61 (s,
3H) ppm;13C NMR (100 MHz, CDCl3) δ 172.53, 161.81, 155.92, 137.13, 134.72,
128.52, 127.39, 127.23, 114.39, 111.11, 95.09, 82.44, 55.37, 48.58, 27.51
ppm; HRMS (m/z) (APCI): calcd for C19H18NO3308.12812 [M+H+]; found 308.12872。
Embodiment 6
N- acetyl group-N- benzyl -3-(4- fluorophenyl) propine amide synthesis:
Will to fluorobenzene acetylene (0. 1 mmol, 0.0120 g), benzyl isonitrile (0.25 mmol, 0.0293 g), sodium acetate
(0.3 mmol, 0.0246 g), H2O(0.1 mmol, 0.0018 g) and Pd (dppf) Cl2(0.01 mmol, 0.0018 g) mixes
Make solvent together in 2.0 mL DMF in 15 mL tube sealings, are added, 60oIt is stirred 2 hours under C；It is whether complete with TLC tracking reaction
Entirely, after having reacted by decompression filter remove solvent, residue through Flash silica column analysis layer purifying (ethyl acetate/petroleum ether=
1:25) obtain alkynyl amide compound (light yellow solid) 4f9.12 mg, yield 76%；
Characterization of The Products1H NMR (400 MHz, CDCl3) δ 7.47 – 7.42 (m, 2H), 7.34 – 7.30 (m,
4H), 7.28 – 7.25 (m, 1H), 7.08 – 7.02 (m, 2H), 5.22 (s, 2H), 2.62 (s, 3H)
ppm; 13C NMR (100 MHz, CDCl3) δ 172.50, 165.39, 162.86, 155.64, 137.05,
135.13, 135.04, 128.66, 127.57, 127.19, 116.42, 116.19, 115.60, 115.56,
93.05, 82.72, 82.70, 48.64, 27.56 ppm; HRMS (m/z) (APCI): calcd for
C18H15FNO2296.10813 [M+H+]; found 296.10798。
Embodiment 7
N- acetyl group-N- benzyl -3-(2- naphthalene) propine amide synthesis:
By 2- naphthalene acetylene (0. 1 mmol, 0.0152 g), benzyl isonitrile (0.25 mmol, 0.0293 g), sodium acetate (0.3
Mmol, 0.0246 g), H2O(0.1 mmol, 0.0018 g) and Pd (dppf) Cl2(0.01 mmol, 0.0018 g) is mixed in 15
In mL tube sealing, 2.0 mL acetonitrile as solvents are added, 60oIt is stirred 2 hours under C；It is whether complete with TLC tracking reaction, wait react
It is filtered after complete by decompression and removes solvent, residue is obtained through Flash silica column analysis layer purifying (ethyl acetate/petroleum ether=1:25)
12.31 mg of alkynyl amide compound (light yellow solid) 4g, yield 81%；
Characterization of The Products1H NMR (400 MHz, CDCl3) δ 7.99 (s, 1H), 7.81 (dd, J = 12.8,
5.0 Hz, 3H), 7.53 (ddd, J = 10.9, 6.3, 3.6 Hz, 2H), 7.43 (dd, J = 8.5, 1.5
Hz, 1H), 7.38 – 7.33 (m, 4H), 7.31 – 7.26 (m, 1H), 5.28 (s, 2H), 2.65 (s, 3H)
ppm; 13C NMR (100 MHz, CDCl3) δ 172.53, 155.74, 137.12, 134.17, 133.95,
132.54, 128.63, 128.53, 128.19, 127.89, 127.82, 127.52, 127.31, 127.12,
116.52, 94.63, 82.98, 48.67, 27.58 ppm; HRMS (m/z) (ESI): calcd for
C22H18NO2328.13321 [M+H+]; found 328.13223。
Embodiment 8
The synthesis of N- acetyl group-N- benzyl -3- cyclopropyl propine amide:
By cyclopropyl acethlene (0. 1 mmol, 0.0066 g), benzyl isonitrile (0.25 mmol, 0.0293 g), sodium acetate
(0.3 mmol, 0.0246 g), H2O(0.1 mmol, 0.0018 g) and Pd (OAc)2 (0.01 mmol, 0.0024 g) mixes
In 15 mL tube sealings, 2.0 mL DMF are added and make solvent, 60oIt is stirred 2 hours under C；It is whether complete with TLC tracking reaction,
After having reacted by decompression filter remove solvent, residue through Flash silica column analysis layer purifying (ethyl acetate/petroleum ether=1:
25) 4.88 mg of alkynyl amide compound (pale yellowish oil) 4h, yield 74% are obtained；
Characterization of The Products1H NMR (400 MHz, CDCl3) δ 7.34 – 7.29 (m, 2H), 7.26 (t, J =
6.2 Hz, 3H), 5.11 (s, 2H), 2.56 (s, 3H), 1.43 – 1.35 (m, 1H), 0.98 – 0.92 (m,
2H), 0.84 – 0.77 (m, 2H) ppm; 13C NMR (100 MHz, CDCl3) δ 172.58, 155.56,
137.18, 128.45, 127.32, 127.09, 101.72, 70.87, 48.48, 27.55, 9.52, -0.22 ppm;
HRMS (m/z) (APCI): calcd for C15H16NO2242.11756 [M+H+]; found 242.11694。
Embodiment 9
The synthesis of N- propiono-N- benzyl -3- phenyl propyne amide:
By phenylacetylene (0. 1 mmol, 0.0102 g), benzyl isonitrile (0.25 mmol, 0.0293 g), sodium propionate (0.3
Mmol, 0.0229 g), H2O(0.1 mmol, 0.0018 g) and Pd (dppf) Cl2(0.01 mmol, 0.0018 g) is mixed in 15
In mL tube sealing, 2.0 mL acetonitrile as solvents are added, 60oIt is stirred 2 hours under C；It is whether complete with TLC tracking reaction, wait react
It is filtered after complete by decompression and removes solvent, residue is obtained through Flash silica column analysis layer purifying (ethyl acetate/petroleum ether=1:25)
8.26 mg of alkynyl amide compound (yellow solid) 4i, yield 81%；
Characterization of The Products1H NMR (400 MHz, CDCl3) δ 7.44 (dd, J = 13.7, 7.3 Hz, 3H),
7.37 – 7.29 (m, 6H), 7.29 – 7.24 (m, 1H), 5.24 (s, 2H), 3.01 (q, J = 7.2 Hz,
2H), 1.17 (t, J = 7.2 Hz, 3H) ppm; 13C NMR (100 MHz, CDCl3) δ 176.43, 155.54,
137.10, 132.62, 130.85, 128.58, 128.50, 127.37, 127.16, 119.37, 93.73, 82.77,
48.77, 32.94, 8.93 ppm; HRMS (m/z) (APCI): calcd for C19H18NO2292.13321 [M+H+];
found 292.13593。
Embodiment 10
N- acetyl group-N-(4- methoxyphenyl) -3- phenyl propyne amide synthesis:
By phenylacetylene (0. 1 mmol, 0.0102 g), 4- methoxybenzene isonitrile (0.25 mmol, 0.0333 g), acetic acid
Sodium (0.3 mmol, 0.0246 g), H2O(0.1 mmol, 0.0018 g) and Pd (dppf) Cl2(0.01 mmol, 0.0018 g)
It is mixed in 15 mL tube sealings, 2.0 mL DMF is added and make solvent, 60oIt is stirred 2 hours under C；It is whether complete with TLC tracking reaction
Entirely, after having reacted by decompression filter remove solvent, residue through Flash silica column analysis layer purifying (ethyl acetate/petroleum ether=
1:25) obtain 7.34 mg of alkynyl amide compound (yellow oily) 4j, yield 72%；
Characterization of The Products1H NMR (400 MHz, CDCl3) δ 7.37 (dd, J = 4.9, 3.7 Hz, 1H), 7.29
(d, J = 7.9 Hz, 2H), 7.21 – 7.15 (m, 4H), 7.02 – 6.98 (m, 2H), 3.86 (s, 3H),
2.63 (s, 3H) ppm; 13C NMR (100 MHz, CDCl3) δ 172.57, 159.94, 154.93, 132.91,
130.88, 130.74, 130.49, 128.41, 119.51, 114.55, 96.12, 82.84, 55.51, 27.24
ppm; HRMS (m/z) (APCI): calcd for C18H16NO3294.11247 [M+H+]; found 294.11276。
Embodiment 11
The synthesis of N- benzyl-N- benzoyl -3- phenyl propyne amide:
By phenylacetylene (0. 1 mmol, 0.0102 g), benzyl isonitrile (0.25 mmol, 0.0293 g), sodium benzoate (0.3
Mmol, 0.0102 g), H2O(0.1 mmol, 0.0018 g) and Pd (dppf) Cl2(0.01 mmol, 0.0018 g) is mixed in 15
In mL tube sealing, 2.0 mL acetonitrile as solvents are added, 60oIt is stirred 2 hours under C；It is whether complete with TLC tracking reaction, wait react
It is filtered after complete by decompression and removes solvent, residue obtains alkynes acyl through Flash silica column analysis layer purifying (ethyl acetate/petroleum ether)
8.87 mg of amine compounds (light yellow solid) 4k, yield 87%；
Characterization of The Products1H NMR (400 MHz, CDCl3) δ 7.58 (d, J = 7.3 Hz, 2H), 7.38 (t, J
= 7.4 Hz, 3H), 7.30 (t, J = 7.5 Hz, 2H), 7.23 (t, J = 7.4 Hz, 3H), 7.17 (d, J
= 7.2 Hz, 1H), 7.11 (t, J = 7.7 Hz, 2H), 6.95 (d, J = 7.4 Hz, 2H), 5.10 (s,
2H) ppm; 13C NMR (100 MHz, CDCl3) δ 173.01, 154.82, 136.75, 135.90, 132.56,
132.49, 130.50, 129.16, 128.50, 128.43, 128.41, 128.18, 127.61, 119.18,
95.87, 82.67, 48.45 ppm; HRMS (m/z) (APCI): calcd for C23H18NO2340.13321 [M+H+]; found 240.13458。
Claims (2)
1. a kind of synthetic method of alkynyl amide class compound, which is characterized in that synthetic method general formula is as follows:
Wherein, R1=aryl, cyclopropyl；
R2=benzyl
R3=alkyl, aryl；
Catalyst are as follows: Pd (dppf) Cl2；
Solvent are as follows: acetonitrile；
The universal synthesis method of the alkynyl amide class compound is:
By (1) 0.1 mmol of acetylene compound, (2) 0.25 mmol of benzyl isonitrile, organic acid sodium (3) 0.3 mmol, H2O 0.1
Mmol and 0.01 mmol of catalyst are mixed in 15 mL tube sealings, and 2.0 mL solvents are added, stir 2 hours at 60 DEG C；With
Whether TLC tracking reaction is complete, filters after having reacted by decompression and removes solvent, and residue is purified through Flash silica column analysis layer
Obtain alkynyl amide compound.
2. the synthetic method of alkynyl amide class compound according to claim 1, which is characterized in that the Flash silica column layer
Analysis purifying, eluant, eluent are ethyl acetate/petroleum ether=1: 25.
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| CN107056635A (en) | 2017-08-18 |
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