CN111808072B - Synthetic method of 3-formyl indole derivative - Google Patents

Synthetic method of 3-formyl indole derivative Download PDF

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CN111808072B
CN111808072B CN202010682527.2A CN202010682527A CN111808072B CN 111808072 B CN111808072 B CN 111808072B CN 202010682527 A CN202010682527 A CN 202010682527A CN 111808072 B CN111808072 B CN 111808072B
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黄乐浩
金红蕾
徐孟华
杨慧慧
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Wenzhou Medical University
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
    • C07D471/06—Peri-condensed systems

Abstract

The invention discloses a synthetic method of a 3-formyl indole derivative, which comprises the following steps: under the action of a palladium catalyst and an oxidant, 3- (dimethylamino) -1- (2-pyridyl) -2-propenone reacts with N-substituted aniline in a solvent, and after the reaction is finished, the 3-formyl indole derivative is obtained through post-treatment. The method is based on a C-H/C-H cross dehydrogenation coupling strategy as a key step, and can be used for simply and conveniently synthesizing 7 3-formyl indole derivatives with potential activity, and raw materials used in the method are cheap, simple and easily available.

Description

Synthetic method of 3-formyl indole derivative
Technical Field
The invention belongs to the field of organic synthesis, and particularly relates to a synthetic method of a 3-formyl indole derivative.
Background
Indole rings are structural units with very high application value and are widely present in perfumes, pesticides, coal tar, essential oil and dyes. In addition, the effects of simple derivatives such as neurotransmitter serotonin, composite alkaloids such as anticancer drugs vinblastine and mitomycin C used in clinic, antihypertensive alkaloid reserpine and indole derivatives in the field of medicine are not ignored. Among them, the 3-formyl indole derivatives exhibit wide pharmacological activity and are applied to the treatment of various diseases such as antiemetic, antihypertensive, antitumor, anti-inflammatory and antidepressant.
With the intensive knowledge of the use of indole compounds, the research on the synthesis method of indole ring compounds is increasing, and a plurality of reports on the synthesis method are reported every year. Meanwhile, transition metal catalyzed C-H/C-H cross dehydrogenation coupling reactions play an increasingly important role in organic synthesis. In 2008, Frank glorious professor reports a mode of synthesizing an indole ring structure by direct oxidative coupling, and realizes the process of synthesizing indole by intramolecular cyclization reaction of (Z) -3- (anilino) butyl-2-methyl enoate. This method requires the prior synthesis of a (Z) -3- (anilino) but-2-enoic acid methyl ester substrate and is not highly reactive with certain substrates containing heterocyclic rings, such as pyridine rings.
Disclosure of Invention
The invention provides a synthesis method of a 3-formyl indole derivative, which can synthesize the 3-formyl indole derivative by one step by using cheap and easily available raw materials, and a substrate can contain a pyridine ring.
A method for synthesizing a 3-formylindole derivative, comprising:
under the action of a palladium catalyst and an oxidant, 3- (dimethylamino) -1- (2-pyridyl) -2-propenone reacts with N-substituted aniline in a solvent, and after the reaction is finished, the 3-formyl indole derivative is obtained through post-treatment;
the structure of the 3- (dimethylamino) -1- (2-pyridyl) -2-propenone is shown as a formula (II):
Figure BDA0002586356970000021
the structure of the N-substituted aniline is shown as the following formula:
Figure BDA0002586356970000022
the structure of the 3-formyl indole derivative is shown as the formula (I):
Figure BDA0002586356970000023
in the formulae (I) and (III), R1Selected from H, halogen, C1～C4Alkyl or C1～C4An alkoxy group;
R2is selected from C1～C4An alkyl group.
In the present invention, the palladium catalyst, the oxidizing agent and the solvent have a large influence on the reaction, and preferably, the palladium catalyst is palladium acetate.
Preferably, the oxidant is copper acetate or silver acetate.
Preferably, the solvent is trifluorotoluene.
In the present invention, R1Preferably H, F, methyl or methoxy.
R2Preferably methyl or ethyl.
Preferably, the reaction temperature is 80-100 ℃ and the reaction time is 12-24 hours.
The synthesis method of the 3-formyl indole derivative further comprises the following steps of synthesizing 3- (dimethylamino) -1- (2-pyridyl) -2-propenone:
reacting 2-acetylpyridine with N, N-dimethylformamide dimethyl acetal in toluene to obtain the 3- (dimethylamino) -1- (2-pyridyl) -2-propenone.
Compared with the prior art, the invention has the beneficial effects that:
(1) the starting raw materials are simple and easy to obtain, and the 3-formyl indole derivative can be conveniently obtained through one-step reaction;
(2) the products obtained by the process of the invention are of a wide variety and may contain heterocyclic groups.
Detailed Description
The invention is further described with reference to specific examples.
The main instruments used in the invention are as follows:
avance III 500MHz NMR spectrometer (Bruker, Switzerland); avance III 400MHz NMR spectrometer (Bruker, Switzerland); ESI-Q-TOF high resolution mass spectrometer (Waters, USA);
Figure BDA0002586356970000031
X-4B micro melting point apparatus (Shanghai apparatus electro-physical optics apparatus Co., Ltd.).
The main reagents are as follows:
2-acetylpyridine, N-dimethylformamide dimethyl acetal, N-alkyl aromatic amines (sahn chemical technology (shanghai) ltd); palladium acetate (alfa aesar chemical ltd); all other reagents are domestic analytical purifiers and are directly used without treatment; column chromatography silica gel was purchased from Qingdao ocean chemical company.
The general reaction scheme for the synthesis of 3-formylindole derivatives (3a-3g) according to the invention is as follows:
Figure BDA0002586356970000032
3a.R1＝H,R2＝CH3；3b.R1＝p-CH3,R2＝CH3；3c.R1＝p-OCH3,R2＝CH3；3d.R1＝p-F,R2＝CH3；3e.R1＝m-CH3,R2＝CH3；3f.R1＝H,R2＝CH2CH3
example 1
(1) Synthesis of 3- (dimethylamino) -1- (2-pyridyl) -2-propenone (2)
A100 mL round bottom flask was charged with 5.02g (41.5mmol) of 2-acetylpyridine, 10.36g (87mmol) of N, N-dimethylformamide dimethyl acetal, dissolved completely in 25mL of toluene, refluxed at 120 ℃ for 12h, and spotted to determine whether the reaction was complete. And after the reaction is stopped, carrying out vacuum filtration to obtain a crude product, adding 60mL of normal hexane into the crude product, stirring for 15min, and carrying out vacuum filtration. The filter residue is transferred to 60mL of anhydrous ether and stirred for 15 min. Suction filtration, washing the filter residue with 10mL of anhydrous ether, drying to obtain 6.45g of dark green solid (2, CAS No.75415-00-8), yield 88.3%, m.p.106-107 ℃.1H NMR(500MHz,CDCl3)δ8.63(d,1H,J＝4.5Hz),8.14(d,1H,J＝8.0Hz),7.92(d,1H,J＝12.5Hz),7.80(t,1H,J＝7.75Hz),7.36(t,1H,J＝6Hz),6.45(d,1H,J＝12.5Hz),3.18(s,3H),3.00(s,3H)；13C NMR(100MHz,CDCl3)δ186.8,156.2,154.7,148.2,136.7,125.4,122.0,91.1,45.1,37.4；HRMS(ESI)[M+H]+,C10H12N2O, found (calculated), m/z 177.1022 (177.1022).
(2) Synthesis of 3-formylindole derivative (3)
To a 35mL Schlenk tube were added 0.044g (0.25mmol) of 3- (dimethylamino) -1- (2-pyridyl) -2-propenone (2), 0.107g (1.0mmol) of N-methylaniline (1), 0.006g (0.025mmol) of palladium acetate, 0.0545g (0.3mmol) of copper acetate, 2.5mL of trifluorotoluene, and reacted at 90 ℃ for 24 h. After completion of the reaction, the reaction system was cooled to room temperature, concentrated and subjected to column chromatography (V (ethyl acetate): V (petroleum ether) ═ 1:3) to obtain compound 3a (Reaxys ID: 9483414).
The structural characterization data is as follows:
3- (1-methyl-1H-indolyl) -2-pyridinyl-methanone 3a as a tan solid, yield 29%, m.p.102-103 ℃.1H NMR(400MHz,CDCl3)δ8.76(s,1H),8.75(d,1H,J＝4.8Hz),8.64(d,1H,J＝6.8Hz),8.21(d,1H,J＝8Hz),7.92(t,1H,J＝7.8Hz),7.49(t,1H,J＝5.6Hz),7.39(m,3H),3.92(s,3H)；13C NMR(100MHz,CDCl3)δ186.3,156.8,148.0,140.6,137.1,137.0,128.2,125.7,123.6,123.4,123.0,122.9,113.8,109.5,33.6；HRMS(ESI)[M+H]+,C15H12N2O, found (calculated), m/z 237.1029 (237.1022).
EXAMPLES 2-7 Synthesis of Compound 3b-3g
The conditions of the synthesis method are the same as those of the compound 3a, except that the reaction substrates are different, and the reaction substrates can be referred to a general reaction formula to obtain the compounds 3b-3g respectively.
The product obtained is characterized by the following data and yields
3- (1, 5-dimethyl-1H-indolyl) -2-pyridinyl-methanone 3b as a brownish yellow liquid in 29% yield.1H NMR(500MHz,CDCl3)δ8.67(d,1H,J＝4.5Hz),8.66(s,1H),8.43(s,1H),8.15(d,1H,J＝8Hz),7.86(t,1H,J＝7.5Hz),7.43(t,1H,J＝6.5Hz),7.24(d,1H,J＝8Hz),7.15(d,1H,J＝8.5Hz),3.82(s,3H),2.52(s,3H)；13C NMR(125MHz,CDCl3)δ186.3,157.0,148.0,140.6,137.0,135.4,132.5,128.4,125.6,124.9,123.5,122.8,113.5,109.2,33.6,21.6；HRMS(ESI)[M+H]+,C16H14N2O, found (calculated), m/z 251.1177 (251.1179).
3- (1-methyl-5-methoxy-1H-indolyl) -2-pyridinyl-methanone 3c (CAS No.59908-55-3) as a tan solid, yield 33%, m.p.101-102 ℃.1H NMR(400MHz,CDCl3)δ8.74(d,1H,J＝8Hz),8.72(s,1H),8.20(d,1H,J＝7.6Hz),8.17(d,1H,J＝2.4Hz),7.92(t,1H,J＝7.8Hz),7.48(t,1H,J＝6.2Hz),7.29(s,1H),7.01(d,1H,J＝8.8Hz),3.98(s,3H),3.89(s,3H)；13C NMR(125MHz,CDCl3)δ186.2,156.9,156.8,148.0,140.6,137.0,132.0,129.1,125.6,123.5,121.4,113.8,110.3,104.4,55.8,33.7；HRMS(ESI)[M+H]+,C16H14N2O2Found (calculated value), m/z 267.1144 (267.1128).
3- (1-methyl-5-fluoro-1H-indolyl) -2-pyridyl-methanone 3d, yellow brown needle crystal, yield 20%, m.p.92-93 ℃.1H NMR(500MHz,CDCl3)δ8.82(s,1H),8.75(d,1H,J＝6Hz),8.33(d,1H,J＝12Hz),8.21(d,1H,J＝9.5Hz),7.94(t,1H,J＝9.5Hz),7.51(t,1H,J＝4.75Hz),7.32(t,1H,J＝7.5Hz),7.12(t,1H,J＝11Hz),3.92(s,3H)；13C NMR(125MHz,CDCl3)δ185.0,159.1(d,J＝243.9Hz),155.5,147.1,140.5,136.1,132.5,128.0(d,J＝10.9Hz),124.8,122.5,112.8(d,J＝4.5Hz),110.6(d,J＝27Hz),109.3(d,J＝10Hz),107.5(d,J＝25.9Hz),32.8；HRMS(ESI)[M+H]+,C15H11FN2O, found (calculated), m/z 255.0929 (255.0928).
3- (1, 6-dimethyl-1H-indolyl) -2-pyridinyl-methanone 3e as a tan solid, yield 16%, m.p.96-97 ℃.1H NMR(500MHz,CDCl3)δ8.75(d,1H,J＝6Hz),8.69(s,1H),8.51(d,1H,J＝10Hz),8.21(d,1H,J＝10Hz),7.93(t,1H,J＝9.75Hz),7.49(t,1H,J＝7.5Hz),7.24(d,1H,J＝10Hz),7.21(s,1H),3.89(s,3H),2.57(s,3H)；13C NMR(125MHz,CDCl3)δ186.2,156.9,148.0,140.2,137.4,137.0,133.4,125.9,125.6,124.5,123.5,122.7,113.9,109.6,33.5,21.9；HRMS(ESI)[M+H]+,C16H14N2O, found (calculated), m/z 251.1178 (251.1179).
3- (1-Ethyl-1H-indolyl) -2-pyridinyl-methanone 3f as a yellow liquid in 17% yield.1H NMR(500MHz,CDCl3)δ8.71(s,1H),8.63(d,1H,J＝4Hz),8.54(d,1H,J＝7Hz),8.09(d,1H,J＝8Hz),7.79(t,1H,J＝7.75Hz),7.36(t,1H,J＝6Hz),7.27(m,3H),4.17(q,2H,J＝7.5Hz),1.46(t,3H,J＝7Hz)；13C NMR(125MHz,CDCl3)δ185.3,155.9,147.1,138.0,136.0,135.1,127.4,124.6,122.5,122.2,122.1,121.8,113.0,108.6,40.9,14.2；HRMS(ESI)[M+H]+,C16H14N2O, found (calculated), m/z 251.1178 (251.1179).
1- (5, 6-dihydro-4H-pyrrolo [3,2, 1-IJ)]3g of quinolyl) -2-pyridyl-methanone was a brown yellow liquid with a yield of 40%.1H NMR(400MHz,CDCl3)δ8.74(m,2H),8.33(d,1H,J＝7.6Hz),8.21(d,1H,J＝8.0Hz),7.91(t,1H,J＝7.8Hz),7.47(t,1H,J＝6.0Hz),7.29(t,1H,J＝7.6Hz),7.07(d,1H,J＝6.8Hz),4.27(t,2H,J＝5.8Hz),3.05(t,2H,J＝6.0Hz),2.30(m,2H)；13C NMR(125MHz,CDCl3)δ186.4,156.9,148.0,137.5,137.0,134.2,126.2,125.5,123.5,123.2,122.0,120.7,120.5,114.3,44.9,24.4,22.8；HRMS(ESI)[M+H]+,C17H14N2O, found (calculated), m/z 263.1176 (263.1179).
Examples 8 to 23
The synthesized product was the same as in example 1 except that the reaction conditions in step (2) were changed, and the reaction conditions and the reaction results are shown in Table 1 below.
TABLE 1 Effect of step (2) reaction conditions
Figure BDA0002586356970000061
N.d means no product was detected.
As is clear from Table 1, the reaction did not proceed unless silver acetate was added; when manganese acetate, silver oxide or copper chloride is added respectively, the reaction efficiency is obviously reduced, and the oxidant has a great influence on the reaction efficiency.
When palladium chloride or palladium (II) trifluoroacetate is used as a catalyst instead of palladium acetate, the reaction activity is not as good as that of palladium acetate, and when palladium acetate is not added, the reaction can not occur at all, so that the catalyst has a great influence on the efficiency of the reaction.
When toluene and xylene are respectively used as solvents instead of trifluorotoluene, the reaction efficiency is slightly reduced; when N, N-dimethylformamide and 1, 2-dichloroethane, which are relatively polar, are used, the reaction efficiency is significantly reduced, even expressed as complete inhibition, and it can be seen that the solvent also has a large influence on the efficiency of the reaction.
When the reaction temperature is increased, the reaction efficiency is slightly decreased, and when the reaction temperature is decreased, the reaction efficiency is significantly decreased, so that the reaction temperature also has a large influence on the reaction efficiency.

Claims (5)

1. A method for synthesizing a 3-formylindole derivative, which comprises the following steps:
under the action of a palladium catalyst and an oxidant, 3- (dimethylamino) -1- (2-pyridyl) -2-propenone reacts with N-substituted aniline in a solvent, and after the reaction is finished, the 3-formyl indole derivative is obtained through post-treatment;
the structure of the 3- (dimethylamino) -1- (2-pyridyl) -2-propenone is shown as a formula (II):
Figure DEST_PATH_IMAGE002
（II）
the structure of the N-substituted aniline is shown as the following formula:
Figure DEST_PATH_IMAGE004
（III）
the structure of the 3-formyl indole derivative is shown as the formula (I):
Figure DEST_PATH_IMAGE006
（I）
in the formulae (I) and (III), R1Selected from H, halogen, C1~C4Alkyl or C1~C4An alkoxy group;
R2is selected from C1~C4An alkyl group;
the palladium catalyst is palladium acetate;
the oxidant is copper acetate or silver acetate;
the solvent is trifluorotoluene;
the reaction temperature is 80-100 ℃.
2. The method of synthesizing a 3-formylindole derivative according to claim 1, wherein R is1Selected from H, F, methyl or methoxy.
3. The method of synthesizing a 3-formylindole derivative according to claim 1, wherein R is2Selected from methyl or ethyl.
4. The method for synthesizing a 3-formylindole derivative according to claim 1, wherein the reaction time is 12 to 24 hours.
5. The method of synthesizing a 3-formylindole derivative according to claim 1, further comprising synthesizing 3- (dimethylamino) -1- (2-pyridyl) -2-propenone:
2-acetylpyridine andN,N-dimethyl formamide dimethyl acetal reacts in toluene to obtain the 3- (dimethylamino) -1- (2-pyridyl) -2-propenone.
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Development of novel small molecules for the treatment of ALS;Bini Mathew;《Bioorganic & Medicinal Chemistry Letters》;20200215;第30卷(第4期);表2 *
Palladium Catalyzed C-C and C-N Bond Formation via ortho C-H Activation and Decarboxylative Strategy: A Practical Approach towards N-Acylated Indoles;Saurabh Kumar;《Adv. Synth. Catal.》;20171122;第360卷;表1-2、图2 *
Palladium-Catalyzed Oxidative Coupling of Aromatic Primary Amines and Alkenes under Molecular Oxygen: Stereoselective Assembly of (Z)‑Enamines;Xiaochen Ji;《J. Org. Chem.》;20131027;第78卷;式6 *
Synthesis of Functionalized Indoles via Palladium-Catalyzed Cyclization of N-(2-allylphenyl) Benzamide: A Method for Synthesis of Indomethacin Precursor;Zhe Chang;《Molecules》;20200309;第25卷;全文 *
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