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Preparation method of 2-methyl-7-azaindole

An azaindole and methyl technology, which is applied in the field of preparation of 2-methyl-7-azaindole, can solve the problems of expensive raw material reagents, intense reaction process, harsh production conditions and the like, and achieves low cost, The effect of easy availability of raw materials and mild reaction conditions

Inactive Publication Date: 2012-12-19
ABA CHEM SHANGHAI
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Problems solved by technology

[0014] However, the above-mentioned methods have disadvantages, such as harsh reaction conditions, ultra-low temperature reaction, and expensive raw material reagents.
[0016] However, the reaction process of this method is relatively intense, the production conditions are harsh, and the production has certain risks; at the same time, the reaction yield is quite low

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  • Preparation method of 2-methyl-7-azaindole
  • Preparation method of 2-methyl-7-azaindole
  • Preparation method of 2-methyl-7-azaindole

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Embodiment 1

[0029] Example 1 Preparation of 2-methyl-7-azaindole

[0030] (1) 2-amino-3-picoline is acylated with acetic anhydride to generate 2-acetylamino-3-picoline

[0031] In a 100L reactor, add 10Kg of 2-amino-3-picoline, 40Kg of toluene and 15Kg of acetic anhydride, slowly raise the temperature to 60°C for reaction, react for 2 hours, and monitor and control the raw material <1% by HPLC; cool to 40°C, concentrate under reduced pressure Recover toluene, transfer the residue to a 500L reaction kettle, add 100Kg water to quench, adjust the pH to 10 with sodium carbonate, extract 50Kg×3 with dichloromethane, combine the extracts, wash with saturated saline, dry over anhydrous sodium sulfate, and filter; Concentrate under reduced pressure to dryness (dichloromethane is recovered) to obtain 12.7Kg (92%) of crude product. The crude product can be directly put into the next step of cyclization reaction. Or recrystallize the crude product with 38.1Kg of isopropanol, heat up and reflux to ...

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Abstract

The invention relates to a preparation method of 2-methyl-7-azaindole. The method comprises the steps that: (1) 2-amino-3-methylpyridine is subjected to an acetic anhydride acylation reaction, such that 2-acetamido-3-methylpyridine is produced; and (2) 2-acetamido-3-methylpyridine is subjected to a cyclization reaction under the effects of sodium amide and N-methylaniline, such that 2-methyl-7-azaindole is produced. The method provided by the invention has the advantages of easy-to-obtain raw materials, relatively mild reaction conditions, easy control, high yield (wherein a total yield is higher than 60%), and low cost. The purity of the product 2-methyl-7-azaindole is high (wherein the purity is no lower than 99.5%). The product is suitable for industrialized productions.

Description

technical field [0001] The invention relates to medicinal chemistry, in particular to a preparation method of 2-methyl-7-azaindole. Background technique [0002] 2-Methyl-7-azaindole is a commonly used intermediate in the current synthesis of new drug research-dopamine receptor inhibitors, and its preparation method is mainly as follows: [0003] method one: [0004] [0005] Sandham, David A. et al [0006] Bioorganic & Medicinal chemistry Letter, 19(16), 4794-4798; 2009 [0007] Method Two: [0008] [0009] Armer, Richard E. et al. (GB 2422831) [0010] Method three: [0011] [0012] Estel, L. et al. [0013] Journal of Organic Chemistry, 53(12), 2740-4; 1988 [0014] However, the above-mentioned methods have disadvantages, such as harsh reaction conditions, ultra-low temperature reaction, and expensive raw material reagents. Gao Shu et al. proposed the following synthesis method in Organometallics in 1998 (Gao, Shu et al. Organometallics, 17(21), 4666-4...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D471/04
Inventor 林志刚蔡彤
Owner ABA CHEM SHANGHAI
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