Acetic Acid → N-{2-(2-Cyano-3-oxobut-1-en-1-yl)furo[3,2-c]pyridin-4-yl}benzamide

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Reaction Steps

A mixture of 1.50 g (5.63 mmol) N-(2-formylfuro[3,2-c]pyridin-4-yl)benzamide (Example 3A), 0.65 g (6.2 mmol) sodium (1Z)-1-cyanoprop-1-en-2-olate, 0.4 ml (7.04 mmol) acetic acid and 56 μl (0.56 mmol) piperidine in dry dichloromethane (35 ml) containing 4 Å molecular sieve was stirred under reflux for 1 h. After cooling, 50 ml aq. sodium bicarbonate solution were added, and the mixture was stirred for 1 h at rt. The molecular sieve was filtered off, and the filtrate was concentrated under reduced pressure. The residue was treated with ethyl acetate and saturated aq. sodium carbonate solution. The organic layer was separated, washed with water, dried, and concentrated under reduced pressure to afford the title compound (1.5 g, 80% of th.) as a pale yellow solid which was used in the next step without further purification.

Provenance & Evidence