A Practical Preparation of Methyl 2-Methoxy-6-metholaminopyridine-3-carboxylate from 2, 6-Dichloro-3-trifluoromethylpyridine

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概要

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• An effective and practical synthetic route to methyl 2-methoxy-6-methylaminopyridine-3-carboxylate(7), the key intermediate of 5-bromo-2-methoxy-6-methylaminopyridine-3-carboxylic acid(1), from 2, 6-dichloro-3-trifluoromethylpyridine(12)was undertaken. Process improvements were highlighted by regioselectivity of 12 with a nitrogen nucleophile and conversion of the 3-trifluoromethyl group into the methoxycarbonyl group. The reaction of 12 with N-benzylmethylamine provided the 6-(N-benzyl-N-methyl)aminopyridine 26a and the regioisomer 26b in >98:<2 ratio in a quantitative yield. Treatment of 2-methoxy-6-methylamino-3-trifluoropyridine(14a)with a large excess of sodium methoxide followed by acid hydrolysis gave the pyridine-3-carboxylic ester 7 in an excellent yield. The potential application of this reaction is also described.

• 社団法人日本薬学会の論文
• 2001-12-01

著者

• Kato Satoru

  Kanazawa Univ. Kanazawa Jpn

• 賀登 志朗

  大日本製薬株式会社創薬研究所

• HIROKAWA Yoshimi

  Chemistry Research Laboratories, Dainippon Pharmaceutical Co. Ltd.

• KATO Shiro

  Chemistry Research Laboratories, Dainippon Pharmaceutical Co. Ltd.

• Kato S

  Discovery Research Laboratories I Dainippon Pharmaceutical Co. Ltd.

• Kato S

  Chemistry Research Laboratories Dainippon Pharmaceutical Co. Ltd.

• HORIKAWA Tamaki

  Chemistry Research Laboratories, Dainippon Pharmaceutical Co., Ltd.

• Horikawa T

  Chemistry Research Laboratories Dainippon Pharmaceutical Co. Ltd.

• Hirokawa Y

  Medicinal Chemistry Group Chemistry Research Laboratories Dainippon Pharmaceutical Co. Ltd.

• Kato Satoru

  Department Of Molecular Neurobiology Graduate School Of Medicine University Of Kanazawa

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