Potassium Phosphate, Tribasic → N-(4-nitropyridin-2-yl)cyclopropanecarboxamide

Participants

Reaction Conditions

Reaction Steps

2-Chloro-4-nitro-pyridine (476 mg, 3 mmol), cyclopropanecarboxylic acid amide (306 mg, 3.6 mmol), and tripotassium phosphate (892 mg, 4.2 mmol) are mixed in dimethoxyethane under an argon atmosphere. (2′-Dicyclohexylphosphanyl-biphenyl-2-yl)-dimethyl-amine (118 mg, 0.3 mmol) and Pd2(dba)3 (275 mg, 0.3 mmol) are added and the mixture is stirred for 3 h at 90° C. Further 0.5 equivalent cyclopropanecarboxylic acid amide (128 mg, 1.5 mmol) is added and the mixture is stirred for 1 additional hour. After cooling at RT the reaction mixture is taken in ethyl acetate, washed with a solution of saturated sodium hydrogen carbonate and brine. The combined organic phases are dried (Na2SO4), concentrated under reduced pressure and the residue is purified by column chromatography (ethyl acetate/hexane) to afford the title compound as a brown solid. M-H−=206.1, HPLC tR: 4.62 min.

Provenance & Evidence