Imidazole → 5-bromo-2-((tert-butyldimethylsilyloxy)methyl)-1-methyl-1H-indole

Participants

Reaction Steps

To a solution of (5-bromo-1-methyl-1H-indol-2-yl)methanol (7.8 g, ca. 31.3 mmol) in CH2Cl2 (80 mL) was added imidazole (2.6 g, 38.2 mmol, 1.2 eq) followed by TBS-Cl (5.2 g, 34.5 mmol, 1.1 eq) at 0° C. The reaction was monitored by LC-MS. After 1 h, the reaction was quenched with water then extracted by CH2Cl2 (3×50 mL). The solvent was concentrated to give a crude product which was purified by flash column chromatography (50% CH2Cl2 in hexanes) to afford the title compound (10.7 g, 30.2 mmol, 96%) over three steps as an off-white solid.

Provenance & Evidence