Sodium hydride → 188533-07-5

Participants

Reaction Steps

A 60% dispersion of NaH in mineral oil (1.70 g, 42.5 mmol) was added to a stirred solution of 2,4-dibromo-N-(4-fluorobenzyl)butanamide (10.0 g, 28.3 mmol, intermediate Q) in THF (25 mL) at 0° C. The reaction mixture was allowed to warm to rt and stir for and additional 2 h. The reaction mixture was carefully quenched with ice and diluted with water. The resulting mixture was extracted with EtOAc. The combined organic layers were washed with water and then brine solution. The organic layer was over sodium sulfate, filtered, and concentrated in vacuo. The crude product was purified using silica gel column chromatography (10% EtOAc/hexanes) to afford the desired product (5.90 g, 64% yield): LCMS (ES-API), m/z 272.4, 274.3 (M+H)+; 1H NMR (400 MHz, DMSO-d6) δ ppm 2.12-2.27 (m, 1H) 2.56-2.68 (m, 1H) 3.27 (dd, J=7.78, 3.26 Hz, 2H) 4.29-4.38 (m, 1H) 4.40-4.57 (m, 1H) 4.73 (dd, J=7.03, 3.01 Hz, 1H) 7.04-7.35 (m, 4H).

Provenance & Evidence