Triethylamine → N'-(5-cyano-2-fluoro-phenyl)-N-methyl-hydrazinecarboxylic acid tert-butyl ester

Participants

Reaction Conditions

Reaction Steps

A mixture of N-methyl-hydrazinecarboxylic acid tert-butyl ester (Intermediate 1; 1.00 g, 6.1 mmol), 5-cyano-2-fluorophenylboronic acid (CombiBlocks; 1.00 g, 6.84 mmol), copper(II) acetate (1.1 g, 6.1 mmol) and triethylamine (2.1 mL, 15.1 mmol) in 1,2-dichloroethane (30 mL) was heated in an oil bath at 60° C. for 3 h. The mixture was allowed to cool, and it was then adsorbed onto silica gel and purified by chromatography using an ISCO 120 g column, eluting with 10-50% ethyl acetate/hexanes, to give N′-(5-cyano-2-fluoro-phenyl)-N-methyl-hydrazinecarboxylic acid tert-butyl ester (700 mg, 44%) as a colorless oil.

Provenance & Evidence