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3-cyanogen radical indole compounds and its synthetic method

A cyanoindole and compound technology, which is applied in the field of synthesis of 3-cyanoindole compounds, can solve the problems of difficulty in applying industrialized production, high price of sodium bis(trimethylsilyl)amide, and the like, and achieves an operation method. Simple, low production cost, and reduced effect of separation and purification processes

Active Publication Date: 2008-07-16
CHINA GATEWAY PHARMA DEV CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The sodium bis(trimethylsilyl)amide price that this method adopts is more expensive, is difficult to be applied to suitability for industrialized production

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1～8

[0024] Embodiment 1~8 3-cyanoindole compounds

[0025] Table 1 shows Examples 1-8 of 3-cyanindole compounds represented by formula I.

[0026] Formula I

[0027] Table 1 Examples 1-8 of 3-cyanindole compounds

[0028] Example

R 1

R 2

Example

R 1

R 2

1

H

7-Br

5

H

7-OCH 3

2

H

7-Cl

6

4-CH 3

6-CH 3

3

H

6-F

7

4-CH 3

7-CH 3

4

H

7-F

8

6-CH 3

7-CH 3

[0029] Reference Example 1 Preparation of 5-chloro-3-formylindole

[0030] Add 5-chloroindole (0.1mol), DMF (0.15mol) and dichloroethane (100mL) in turn to the reaction flask at room temperature (25-30°C), then stir and add phosphorus oxychloride (0.15mol) and heat React at 88°C for 18 hours and go directly to TLC to follow the reaction of 5-chloroindole to scale up. After the reaction, the reaction solution was cooled to room temp...

Embodiment 1

[0086] Method Example 1 Preparation of 5-chloro-3-cyanindole

[0087] Add 5-chloro-3-formylindole (01mol), hydroxylamine hydrochloride (0.1mol) and DMF (120mL) sequentially into the reaction flask at room temperature (25-30°C), then stir and heat to 100°C until TLC traces The 5-chloro-3-formylindole reaction disappeared. After the reaction, the reaction solution was cooled to room temperature, added water (100mL), left to stand, filtered, and dried to obtain a light yellow solid with a yield of 86%. The identification result was:

[0088] 1 H NMR (DMSO-d 6 ): δ = 7.42 (1H, dd, J = 1.6, 8.6Hz), 7.50 (1H, d, J = 8.6Hz), 7.80 (1H, d, J = 2.4Hz), 8.34 (1H, d, J = 1.6Hz), 12.40 (1H, broad).

Embodiment 2

[0089] Method Example 2 Preparation of 6-chloro-3-cyanindole

[0090] Add 6-chloro-3-formylindole (0.1mol), hydroxylamine hydrochloride (0.15mol) and DMAc (110mL) successively into the reaction flask at room temperature (25-30°C), then stir and heat to 65°C until TLC The disappearance of the 6-chloro-3-formylindole reaction was followed. After the reaction, the reaction solution was cooled to room temperature, added water (100mL), left to stand, filtered, and dried to obtain a light yellow solid with a yield of 81%. The identification result was:

[0091] 1 H NMR (DMSO-d 6 ): δ = 7.38 (1H, dd, J = 1.6, 8.6Hz), 7.62 (1H, d, J = 8.5Hz), 7.80 (1H, m), 8.29 (1H, s), 12.31 (1H, broad) .

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PUM

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Abstract

The invention discloses a group of novel 3-cyanoindole compounds listed as formula I; wherein, R1 is equal to H, R2 is equal to 7-Br; or R1 is equal to H, R2 is equal to 7-C1; or R1 is equal to H, R2 is equal to 6-F; or R1 is equal to H, R2 is equal to 7-F; or R1 is equal to H, R2 is equal to 7-OCH3; or R1 is equal to 4-CH3, R2 is equal to 6-CH3; or R1 is equal to 4-CH3, R2 is equal to 7-CH3; or R1 is equal to 6-CH3, R2 is equal to 7-CH3. The invention also discloses a synthesis method for the 3-cyano indole compounds listed as formula I. R1 and R2 in formula I are separately H, F, Cl, Br, I, methyl, ethyl, n propyl, isopropyl, butyl, methoxy and benzyloxy, and the steps are that under a temperature of 65 to 180 DEG C, the 3-formylindole compounds and hydroxylamine salt are mixed to be reacted in an organic solvent. The method provided by the invention is easily operated with a low cost and can not only be applied to small-scale facility in a laboratory, but can also be applied to large-scale industrial production.

Description

technical field [0001] The invention relates to a novel 3-cyanindole compound and a synthesis method of the 3-cyanindole compound. Background technique [0002] In the prior art, some of the disclosed 3-cyanindole compounds are widely used as important chemical intermediates in medicine, pesticide and other industries. [0003] M. Maumy (Synthesis, 1989, p451) et al reported a method for generating 3-cyanindole starting from 3-formylindole using ammonium chloride / copper / pyridine / oxygen. The reagent pyridine used in the method is highly toxic, and the post-treatment of the heavy metal copper is difficult, making industrial production difficult. [0004] B.Jiang (Biorg.Med.Chem., 2000, Vol 8, p363) et al. reported using 3-formyl indole as raw material, in (NH 4 ) 2 HPO 4 / CH 3 (CH 2 ) 2 NO 2 Under the system of / acetic acid, make the method for 3-cyanoindole. The nitropropane used in the method is an inflammable and explosive chemical reagent, and the operation is in...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D209/42
Inventor 刘国斌刘军李原强
Owner CHINA GATEWAY PHARMA DEV CO LTD
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