Sodium hydride → HCID 59717607, compound

Participants

Reaction Steps

To a stirred solution of N-(3-Vinyl-pyridin-2-yl)-acetamide 78D (122 mg, 0.75 mmol) and 4-Bromo-2-bromomethyl-1-iodo-benzene (285 mg, 0.75 mmol) in anhydrous DMF (6 mL) under argon was added 95% NaH (21 mg, 0.83 mmol). This mixture was stirred at room temperature for 4.5 h and diluted with saturated NaHCO3 solution. This was extracted with EtOAc (4×60 mL). The combined EtOAc extracts were washed with brine (30 mL), dried (MgSO4), filtered and concentrated in vacuo. This was purified by a ISCO auto CombiFlash with a RediSep 10 g column, eluted with CH2Cl2-EtOAc, detected at 220 nM to give 90 mg of desired N-(5-Bromo-2-iodo-benzyl)-N-(3-vinyl-pyridin-2-yl)-acetamide 78E in 29% yield. HPLC Rt=3.48 min (YMC S5 ODS column 4.6×50 mm, 10-90% aqueous methanol over 4 minutes containing 0.2% phosphoric acid, 4 mL/min, monitoring at 220 nm) LC/MS: M+H=457.

Provenance & Evidence