Sodium hydride → HCID 50912906, compound

Participants

Reaction Conditions

Reaction Steps

A solution of alcohol 82 (242 mg, 0.568 mmol) in anhydrous DMF (5 mL) under N2 at 0° C. was treated with 60% NaH (36 mg, 0.90 mmol), then quickly degassed and resealed under N2. After stirring at 0° C. for 45 min, the reaction was cooled (CO2/acetone), quenched with ice/aqueous NaHCO3 (15 mL), added to brine (40 mL), and extracted with CH2Cl2 (6×50 mL). The combined extracts were evaporated to dryness and the residue was chromatographed on silica gel, eluting with CH2Cl2, to give 1 (171 mg, 87%) as a cream solid: mp (MeOH/CH2Cl2/hexane) 170-172° C.; 1H NMR [(CD3)2SO] δ 8.16 (s, 1H), 7.31 (br dd, J=9.1, 0.8 Hz, 2H), 7.05 (dt, J=9.2, 3.1 Hz, 2H), 5.74 (m, 1H), 4.50 (dd, J=10.8, 8.9 Hz, 1H), 4.46 (dd, J=11.5, 2.8 Hz, 1H), 4.39 (dd, J=11.5, 5.2 Hz, 1H), 4.22 (dd, J=10.8, 6.5 Hz, 1H). Anal. (C13H10F3N3O5) C, H, N.

Provenance & Evidence