Imidazole → 2-Bromo-3-(((tert-butyldimethylsilyl)oxy)methyl)-4-chloropyridine

Participants

Reaction Conditions

Reaction Steps

A mixture of 160b (20 g, 90.0 mmol), tert-butyldimethylchlorosilane (17.6 g, 117 mmol) and imidazole (12.2 g, 180 mmol) in N,N-dimethylformamide (300 mL) was stirred at 15° C. for 12 h. See FIG. 5. TLC (petroleum ether:ethyl acetate=3:1) showed that the starting material was completely consumed. The mixture was diluted with water (200 mL) and extracted with EtOAc (200 mL×2). The organic layers were washed with brine (60 mL), dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (eluting with petroleum ether:ethyl acetate=20:1) to afford 2-bromo-3-(((tert-butyldimethylsilyl)oxy)methyl)-4-chloropyridine 160c (30 g, 99%) as a colorless oil.

Provenance & Evidence