Dimethylformamide → 7-(3-fluoropyridin-4-yl)-5-phenyl-2,3-dihydro-1H-1,4-benzodiazepine

Participants

Reaction Conditions

Reaction Steps

A 5 mL microwave tube was charged with 7-bromo-5-phenyl-2,3-dihydro-1H-1,4-benzodiazepine (50 mg), dimethylformamide (3.5 mL), 3-fluoro-4-pyridylboronic acid (2 equiv), potassium carbonate (2 equiv), bis(triphenylphosphine)-palladiumdichloride (10 mol %), and water (0.7 mL). The mixture was heated in a microwave at 150° C. for 5 min, then cooled and concentrated to dryness. The residue was taken up in ethyl acetate and filtered through a Celite pad. The filtrate was concentrated to dryness and the residue was triturated in diethyl ether. The resulting solids were collected on filter then purified using preparative thin-layer chromatography. The plates were eluted with 12.5% methanol in chloroform, and the desired band was collected to provide 7-(3-fluoropyridin-4-yl)-5-phenyl-2,3-dihydro-1H-1,4-benzodiazepine as a yellow powder. H1 NMR (d6-dmso): 8.45 (d, 1H), 8.32 (d, 1H), 7.52 (d, 1H), 7.46 (m, 2H), 7.36-7.42 (m, 4H), 7.21 (s, 1H), 6.91 (d, 1H), 6.78 (brt, 1H), 3.96 (m, 2H), 3.60 (m, 2H).

Provenance & Evidence