Sodium hydride → HCID 86663364, compound

Participants

Reaction Steps

To a solution of trimethylsulfoxonium iodide (7.10 g, 32.3 mmol) in DMSO (25 mL) were added, sodium hydride (0.774 g, 32.3 mmol, 95%) (portionwise) at ambient temperature, followed by 5-bromonicotinaldehyde (3.00 g, 16.1 mmol) in DMSO (15 mL). The reaction mixture was quenched by the addition of cold ice water (200 mL) and the resulting mixture extracted with ethyl acetate (2×150 mL). The combined organic layer was dried over anhydrous sodium sulfate, filtered and evaporated under reduced pressure to give the residue which was purified by column chromatography using CombiFlash (REDISEP®, silica gel, 40 g, 25% EtOAc/hexanes) to obtain 3-bromo-5-(oxiran-2-yl)pyridine (1.00 g, 31.0%). LCMS Condition B-26: retention time 1.83, [M+2]=202.2. 1H NMR (400 MHz, CDCl3) δ 2.79 (dd, J=2.4 Hz, J=5.2 Hz, 1H), 3.20 (dd, J=4.0 Hz, J=5.2 Hz, 1H), 3.87 (dd, J=2.4 Hz, J=4.0 Hz, 1H), 7.69 (dd, J=1.6 Hz, J=2.0 Hz, 1H), 8.50 (d, J=1.6 Hz, 1H), 8.62 (d, J=2.0 Hz, 1H).

Provenance & Evidence