Water → HCID 86587389, compound

Participants

Reaction Steps

Boron tribromide (18.78 mL of a 1 M solutioin in methylene chloride; 18.78 mmol) in 20 mL of methylene chloride was added under nitrogen dropwise over fifteen minutes to a solution of 2-butyl-1-methyl-1H-indole-3-carboxylic acid (5-bromo-6-methoxy-naphthalen-2-ylmethyl)-methyl-amide (3.09 g, 6.26 mmol), prepared in the previous step, in 125 mL of methylene chloride at dry ice-acetone temperature. After the addition the dry ice-acetone bath was replaced with an ice bath and the stirring continued for 4 h. Water was added to the reaction at ice bath temperature. The organic layer was separated and the aqueous layer extracted three times with methylene chloride. The combined extracts were dried (MgSO4) and the solvent removed under reduced pressure to give 2-butyl-1-methyl-1H-indole-3-carboxylic acid (5-bromo-6-hydroxy-naphthalen-2-ylmethyl)-methyl-amide (3.22 g, 100%) as a brown solid foam, MS m/z: 479 [M+H]+.

Provenance & Evidence