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Method for preparing Invokana key intermediate

An intermediate and key technology, which is applied in the field of key chiral intermediates of canagliflozin for the treatment of diabetes, can solve problems such as the source cost of key intermediates of canagliflozin, and achieve the effect of solving preparation and cost problems

Inactive Publication Date: 2015-03-25
JIANGNAN UNIV
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AI Technical Summary

Problems solved by technology

Mainly solve the problem of source and cost of key intermediates of existing canagliflozin

Method used

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  • Method for preparing Invokana key intermediate
  • Method for preparing Invokana key intermediate
  • Method for preparing Invokana key intermediate

Examples

Experimental program
Comparison scheme
Effect test

Embodiment Construction

[0013] The preparation method of the present invention is further described in detail below by way of examples.

[0014] 1. Preparation of 2-(4-fluorophenyl)thiophene and p-fluorophenylmagnesium bromide

[0015] Reaction formula:

[0016]

[0017] In a 500mL three-necked round-bottomed flask, magnesium chips (1.5g, 61.3mmol) and one grain of iodine were added under nitrogen protection. After the iodine was heated and sublimated, a small amount of tetrahydrofuran and p-fluorobromobenzene were added. After the reaction was initiated, a solution of p-fluorobromobenzene (10.7 g, 61.3 mmol) in tetrahydrofuran (100 mL) was slowly added dropwise. After the reaction was completed, the reaction system 1 was obtained.

[0018]

[0019] In a 500mL round bottom flask, add 2-bromothiophene (10.0g, 61.3mmol), tetrahydrofuran (100mL), NiCl 2 (dppe) (80mg, 1.5mol%), the reaction system 1 was slowly added dropwise at 0-5°C, after the drop was completed, the reaction was stirred overnig...

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Abstract

The invention relates to a method for preparing an Invokana key intermediate. By utilizing a complex of transitional metal nickel, the catalytic cross coupling reaction on 2-bromothiophene and p-fluorophenyl magnesium bromide is realized, and the problem that the existing palladium catalyzing method for synthesizing the Invokana key raw material 2-(4-fluorophenyl) thiophene is high in cost is solved.

Description

Technical field: [0001] The present invention relates to a method for the key chiral intermediate of canagliflozin for the treatment of diabetes: [0002] technical background: [0003] Canagliflozin is a SGLT2 inhibitor developed by Johnson & Johnson [11] for the treatment of type 2 diabetes in adult patients. Two studies presented at the 72nd Annual Scientific Session of the American Diabetes Association (ADA) showed that canagliflozin was more effective in lowering blood sugar in patients with type 2 diabetes than glimepiride and sitagliptin. A number of preclinical and clinical studies have confirmed that it has a significant effect on type 2 diabetes, can significantly improve the blood sugar level of patients, and also has a benign improvement on body weight and blood lipids. Adverse reactions mainly include dose-dependent hyperkalemia and genitourinary tract infection, with an incidence rate of 10%. Hypoglycemia reactions rarely occur. The adverse reactions are ge...

Claims

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Application Information

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IPC IPC(8): C07D333/12
CPCC07D333/12
Inventor 张闯范为正唐春雷王倩楠王稞瓒杨宁红胡小霞张春森冯柏年
Owner JIANGNAN UNIV
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