Dimethylformamide → 6-Fluoroquinoline-4-carbonitrile

Participants

Reaction Steps

A mixture of 4-chloro-6-fluoroquinoline (APOLLO) (1120 mg, 6.17 mmol), zinc cyanide (1450 mg, 12.3 mmol) and palladium (0) tetrakis(triphenylphosphine)(713 mg, 0.617 mmol) in dry DMF (15 ml) was treated with microwave (160° C., 30 min.). The mixture was diluted with ethyl acetate and filtered through a pad of celite. To the filtrate was added toluene (ca.20 ml) and the organic layer was washed with water (×2), brine, dried and concentrated in vacuo to give crude product. The crude product was purified by column chromatography on silica gel (ca. 250 g) with hexane-ethyl acetate (3:1) to give the title compound (880 mg, white solid). 1H NMR (270 MHz, CDCl3) δ ppm 7.60-7.70 (1H, m), 7.75-7.79 (1H, m), 7.81-7.87 (1H, m), 8.20-8.28 (1H, m), 9.00-9.05 (1H, m).

Provenance & Evidence