Trimethylsilyldiazomethane → Methyl 5-[(tert-butoxycarbonyl)amino]-2-fluoropyridine-4-carboxylate

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Reaction Steps

To 44 g of 5-tert-butoxycarbonylamino-2-fluoro-isonicotinic acid in 100 mL of methanol and 300 mL of chloroform at 0° C. was added 200 mL of 2 M (trimethylsilyl)diazomethane in hexanes. After allowing the reaction to warm to ambient temperature and stirring for 2 hours, the solvents were removed and the crude product purified by passing through a plug of silica gel with chloroform. The product was then recrystallized from hexanes to give 32.6 g (73%) of 5-tert-butoxycarbonylamino-2-fluoro-isonicotinic acid, methyl ester: melting point 104-105° C. (decomposed); mass spectrum (m/e): M+H 270.9.

Provenance & Evidence