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Preparation method of 7-(4-bromobenzoyl)-1, 3-dihydro-2H-indole-2-one

A technology of bromobenzoyl and dihydrogen, which is applied in the field of preparation of 7--1,3-dihydro-2H-indol-2-one, can solve the problems of difficult separation and purification, high reaction temperature, long time and the like , to achieve the effect of easy availability of raw materials, simple operation and low cost

Pending Publication Date: 2022-02-08
沈阳海诺威医药科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The disadvantage of this route is that the reaction temperature is high and the time is long during the hydrolysis of phosphoric acid, and the red polymer makes separation and purification difficult

Method used

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  • Preparation method of 7-(4-bromobenzoyl)-1, 3-dihydro-2H-indole-2-one
  • Preparation method of 7-(4-bromobenzoyl)-1, 3-dihydro-2H-indole-2-one
  • Preparation method of 7-(4-bromobenzoyl)-1, 3-dihydro-2H-indole-2-one

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0044] Example 1 3,3-dichloro-7- (4-bromobenzoyl) -1,3-dihydro -2H- indol-2-one:

[0045] After weighing tetrahydrofuran 9kg, 7- (4- bromobenzoyl) indole 1.0kg and 0.1kg 36-38% hydrochloric acid, 0.1kg of water, was added N- chlorosuccinimide 1.5kg, 4 hours, purified water was added crystallization suction, the filter cake was dried to give a pale yellow solid 50 deg.] C 1.16kg, 90% yield. 1 H-NMR (DMSO-D6,600MHz) 7.28 (t, 1H, J = 7.8Hz), 7.56 (dd, 1H, J = 7.9Hz), 7.71 (d, 2H, J = 6.7Hz), 7.80 (d, 2H, J = 6.7Hz), 7.96 (d, 1H, J = 7.4Hz), 11.41 (s, 1H). HRMS (ESI, neg) [M-H] = 384.

Embodiment 2

[0046] Example 2 3,3-dichloro-7- (4-bromobenzoyl) -1,3-dihydro -2H- indol-2-one:

[0047] After weighing tetrahydrofuran 9kg, 7- (4- bromobenzoyl) indole and 36-38% 0.5kg 1.0kg hydrochloric acid, was added N- chlorosuccinimide 1.0kg, 4 hours, add purified water analysis crystal suction, the filter cake was dried to give 50 ℃ 0.9kg pale yellow solid, 70% yield.

Embodiment 3

[0048] Example 3 3,3-dichloro-7- (4-bromobenzoyl) -1,3-dihydro -2H- indol-2-one:

[0049]Tetrahydrofuran 10 kg, 7- (4-bromophenyl) hydrazine 1.0 kg and 1.0 kg of hydrochloric acid, 2.0 kg of water, 2.0 kg of N-chlorobuticimide, and 5 hours after reaction, Purified the fresh crystal filtration, the filter cake was dried with a light yellow solid 1.2 kg, yield 94%.

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Abstract

The invention relates to the field of medicinal chemistry, in particular to a preparation method of 7-(4-bromobenzoyl)-1, 3-dihydro-2H-indole-2-one. The preparation method comprises the steps of (1) carrying out a halogenation reaction on 7-(4-bromobenzoyl) indole in tetrahydrofuran in the presence of an acid so as to prepare 3, 3-dihalogenated-7-(4-bromobenzoyl)-1, 3-dihydro-2H-indole-2-one; and (2) carrying out a reduction reaction on the 3, 3-dihalogenated-7-(4-bromobenzoyl)-1, 3-dihydro-2H-indole-2-one in tetrahydrofuran under the action of acetic acid and zinc powder so as to prepare the 7-(4-bromobenzoyl)-1, 3-dihydro-2H-indole-2-one. The method has the characteristics of easily available raw materials, mild reaction conditions, simplicity in operation, high yield, high purity and suitability for industrial production.

Description

Technical field [0001] The present invention relates to pharmaceutical chemistry, specifically relates to a method for producing a 7- (4-bromobenzoyl) -1,3-dihydro -2H- indol-2-one. Background technique [0002] 7- (4-bromobenzoyl) -1,3-dihydro -2H- indol-2-one are important intermediates in the synthesis of sodium bromate Finland, bromfenac sodium Senju Pharmaceutical Co., Ltd. of Japan is developed by dropwise eye drops on the market, in March 2000, access to the Japanese PMDA approved for marketing for the anterior segment and external eye symptomatic treatment of inflammatory diseases. [0003] [0004] Currently 7- (4-bromobenzoyl) -1,3-dihydro -2H- indol-2-one production method mainly comprises the following two: [0005] A method, U.S. Patent No. US 4126635 and Journal of Medicinal Chemistry, 1990 33 (8), 2296-2304 reported that ethyl 2-bromo-4'-benzophenone, and 2-methylmercapto as raw material, Laid under pivaloyl chloride catalyzed cyclization, reduction by Raney nick...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D209/34
CPCC07D209/34Y02P20/55
Inventor 王绍杰牛新文
Owner 沈阳海诺威医药科技有限公司