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Method for synthesizing 2-amino-3-iodo-5-bromopyridine

A synthetic method, bromopyridine technology, applied in the direction of organic chemistry, can solve the problems of high market price, difficult synthesis, lack of literature and patent reports, etc., and achieve the effects of easy promotion, simple post-processing, and easy control of the reaction

Active Publication Date: 2015-07-08
陕西友帮生物医药科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

This product has great value, its synthesis is difficult, the market price is expensive, lack of literature and related patent reports

Method used

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  • Method for synthesizing 2-amino-3-iodo-5-bromopyridine

Examples

Experimental program
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Effect test

Embodiment 1

[0014]

[0015] In a 100ml round bottom single-necked flask, add 38ml of mixed solvent of ethyl acetate and ethanol, 15ml of ethyl acetate, insert a thermometer, start the magnetic stirrer, and add 17.4g of 2-amino-5-bromopyridine, add N- 39.38 g of iodosuccinimide was reacted at 25°C for 18 hours under continuous stirring. TLC and GC confirmed that the reaction of 2-amino-5-bromopyridine was complete. The solvent was removed by rotary evaporation to obtain a crude product, which was recrystallized with a mixed solvent of n-hexane and ethanol to obtain the pure product 2-amino-3-iodo-5-bromopyridine. After drying, the calculated yield was 80.3%, and the purity detected by GC was 97.2%. . NMR analysis: 1HMR(CDCl3)400MHz: δ7.98(s,1H); δ7.66(s,1H); δ4.96(bs,2H)

Embodiment 2

[0017] Add 1006ml of solvent N,N-dimethylformamide to a 2L round-bottom single-necked flask, insert a thermometer and start a magnetic stirrer, and add 348g of 2-amino-5-bromopyridine, and add N-iodosuccinyl 994 g of imines were reacted for 11 hours at a reaction temperature of 36° C. under continuous stirring. TLC and GC confirmed that the reaction of 2-amino-5-bromopyridine was complete. The solvent was removed by rotary evaporation to obtain a crude product, which was recrystallized from a mixed solvent of ethyl acetate and dichloromethane to obtain the pure product 2-amino-3-iodo-5-bromopyridine. After drying, the calculated yield was 79.53%, and the purity was detected by GC 98.7%. NMR analysis: 1HMR(CDCl3)400MHz: δ7.98(s,1H); δ7.66(s,1H); δ4.96(bs,2H)

Embodiment 3

[0019] Add 7500ml of ethanol to a 10L reaction kettle, insert a thermometer to start a mechanical stirrer, and add 3828g of 2-amino-5-bromopyridine, add 12375g of N-iodosuccinimide, and continue at a reaction temperature of 40°C The reaction was stirred for 9 hours. TLC and GC confirmed that the reaction of 2-amino-5-bromopyridine was complete. The solvent was removed by rotary evaporation to obtain a crude product, which was recrystallized from a mixed solvent of ethyl acetate and ethanol to obtain the pure product 2-amino-3-iodo-5-bromopyridine. After drying, the calculated yield was 86.4%, and the purity detected by GC was 97.4%. %. NMR analysis: 1HMR(CDCl3)400MHz: δ7.98(s,1H); δ7.66(s,1H); δ4.96(bs,2H)

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Abstract

The invention relates to a method for synthesizing 2-amino-3-iodo-5-bromopyridine. The method comprises the steps of enabling 2-amino-5-bromopyridine and N-iodo succinimide, which serve as raw materials and are in the mass ratio of 1: (1.7-3.5), to react at the temperature of 23-115 DEG C in a proper solvent so as to produce 2-amino-3-iodo-5-bromopyridine, and purifying, thereby obtaining a pure product 2-amino-3-iodo-5-bromopyridine. According to the method, the raw materials are relatively easily obtained and are reasonable in price; meanwhile, during preparation reaction, no heavy metal and corrosive gas are used, the reaction is mild, no special requirements on reaction equipment is required, and ordinary corrosion-resistant equipment can be applied to production; in addition, reaction conditions of the method are moderate.

Description

(1) Technical field [0001] The invention belongs to the field of organic synthesis, and in particular relates to a synthesis method of 2-amino-3-iodo-5-bromopyridine. (2) Background technology [0002] 2-Amino-3-iodo-5-bromopyridine can be used to synthesize tyrosine kinase inhibitors to treat cancer or prevent the spread of cancer cells, including breast cancer, colon cancer, prostate cancer, lung cancer, gastric cancer, ovarian cancer, Endometrial cancer, kidney cancer, liver cancer, thyroid cancer, uterine cancer, esophageal cancer, squamous cell carcinoma, leukemia, osteosarcoma, melanoma, glioblastoma, neuroblastoma; can be used to synthesize CRAC inhibitors , to treat autoimmune and inflammatory diseases. It can be used as the structural active center of antimalarial drugs; it can be used as a structural scaffold for mitotic kinase inhibitors to achieve effective selective regulation in cells; it can also be used as a Fabl inhibitor to efficiently inhibit the growth o...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D213/73
CPCC07D213/73
Inventor 邓素曼韩猛来新胜曹惊涛
Owner 陕西友帮生物医药科技有限公司
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