Sodium hydride → HCID 68709159, compound

Participants

Reaction Steps

(1-Methylpyrrolidin-3-yl)methanol (0.500 g, 4.34 mmol) was dissolved in dry DMF (8 mL), cooled (<0° C.), NaH (0.260 g, 6.51 mmol, 55% in oil) added and stirred for 30 minutes. 3-Fluorobenzonitrile (0.552 g, 4.56 mmol) was added and the reaction mixture allowed to warm to r.t. over 1 h. Due to excessive foaming the reaction mixture was diluted with dry DMF to 20 mL and stirred over night at r.t. The reaction was quenched by addition of water portionwise, and the mixture was extracted with DCM. The organic phase was dried over a phase separator and concentrated in vacuo. The product was purified by flash chromatography using a step gradient of EtOAc:MeOH:TEA (100:10:2) in EtOAc to give the title compound as an oil. Yield: 0.573 g (58%). 1H NMR (400 MHz, CDCl3) δ 7.30-7.35 (m, 1H), 7.18-7.22 (m, 1H), 7.09-7.12 (m, 1H), 7.07-7.09 (m, 1H), 3.86 (d, 2H, J=6.95 Hz), 2.54-2.67 (m, 3H), 2.40-2.51 (m, 2H), 2.33 (s, 3H), 2.00-2.10 (m, 1H), 1.51-1.61 (m, 1H).

Provenance & Evidence