Benzyl Bromide → HCID 71284415, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of methyl 4-hydroxy-1-methyl-1H-indole-5-carboxylate (7.70 g, 37.52 mmol), prepared according to the literature (Bioorg. Med. Chem. 2005, 13, 1497-1505), in CH3CN (150 mL) was added K2CO3 (8.80 g, 63.67 mmol), NaI (200 mg, cat.) and BnBr (6.70 mL, 56.41 mmol). The mixture was heated at 70° C. overnight. The solids were filtered off and the mother liquor was concentrated. The residue was purified by column chromatography using EtOAc/hexanes (gradient 10-30%) to afford methyl 4-(benzyloxy)-1-methyl-1H-indole-5-carboxylate (7.10 g) in 85% yield based on recovered starting material (1.90 g).

Provenance & Evidence