N-{2-(2-Cyano-3-oxobut-1-en-1-yl)furo[3,2-c]pyridin-4-yl}benzamide → N-{2-[3,5-Dicyano-2-(difluoromethyl)-6-methyl-1,4-dihydropyridin-4-yl]furo[3,2-c]pyridin-4-yl}-benzamide

Participants

Reaction Steps

A mixture of 200 mg (0.604 mmol) N-{2-(2-cyano-3-oxobut-1-en-1-yl)furo[3,2-c]pyridin-4-yl}benzamide (Example 4A) and 285 mg (2.41 mmol) 3-amino-4,4-difluorobut-2-enenitrile [obtainable by Thorpe reaction of acetonitrile with 2,2-difluoroacetonitrile, cf. Org. React. 15, 1 (1967), ibid. 31, 1 (1984)] in 2-propanol (1 ml) was stirred at reflux for 12 h. Upon cooling, the mixture was concentrated under reduced pressure, and the residue was directly purified by preparative RP-HPLC (acetonitrile/water+0.1% TFA gradient, final mixture 90:10 v/v) to yield 176 mg (67% of th.) of the racemic title compound.

Provenance & Evidence