Dimethylformamide → HCID 86649376, compound

Participants

Reaction Steps

NaH (60% in mineral oil, 90 mg, 2.25 mmol) was added at 0° C. to a stirred mixture of [1-(2-chlorophenyl)-5-{5-[3-(methylsulfonyl)phenyl]-2-thienyl}-1H-pyrazol-3-yl]methanol (222 mg, 0.5 mmol), 2-(bromomethyl)pyridine hydrobromide (190 mg, 0.75 mmol), and anhydrous DMF (5 mL) under N2, the resulting mixture was stirred at it for 4 h. The reaction mixture was poured into ice-water, and extracted with EtOAc. The combined extracts were washed with brine, dried over Na2SO4, and evaporated in vacuo. The crude product was purified by flash chromatography (0-100% EtOAc/hexanes) to give the title compound as a colorless semi-solid (179 mg, 67%). 1HNMR (CDCl3): δ 8.58 (m, 1H), 8.04 (m, 1H), 7.82 (m, 1H), 7.74-7.71 (m, 2H), 7.57-7.44 (m, 6H), 7.20 (m, 2H), 6.76 (m, 2H), 4.78 (m, 4H), 3.08 (s, 3H). MS(ES): 536 [M+H]+.

Provenance & Evidence