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

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 reg...

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Veröffentlicht in:	Chemical & pharmaceutical bulletin 2001, Vol.49(12), pp.1621-1627
Hauptverfasser:	HORIKAWA, Tamaki, HIROKAWA, Yoshimi, KATO, Shiro
Format:	Artikel
Sprache:	eng
Schlagworte:	2,6-dichloro-3-trifluoropyridine 2-chloro-6-methylamino-3-trimethoxymethylpyridine antiemetic agent Antiemetics - chemical synthesis Azepines - chemical synthesis Chemistry Chromatography, High Pressure Liquid dopamine D2,D3 receptor Exact sciences and technology Heterocyclic compounds Heterocyclic compounds with only one n hetero atom and condensed derivatives Indicators and Reagents Magnetic Resonance Spectroscopy Mass Spectrometry Nicotinic Acids - chemical synthesis Organic chemistry Preparations and properties Pyridines - chemical synthesis Pyridines - chemistry regioselective synthesis serotonin-3 receptor Spectrometry, Mass, Fast Atom Bombardment Spectrophotometry, Infrared
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Zusammenfassung:	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:
ISSN:	0009-2363 1347-5223
DOI:	10.1248/cpb.49.1621