Potassium Carbonate → HCID 12083568, compound

Participants

Reaction Steps

A mixture of 2-butyl-benzofuran-3-carboxylic acid (5-bromo-6-hydroxy-naphthalen-2-ylmethyl)-methyl-amide (0.5587 g, 1.2 mmol), prepared in the previous step, bromoacetonitrile (0.10 mL, 1.44 mmol) and potassium carbonate (0.83 g, 6 mmol) in 10 mL of DMF was stirred under nitrogen at room temperature for 18 h (overnight). The reaction was diluted with ethyl acetate and extracted multiple times with water. The organic layer was dried (MgSO4) and the solvent removed under reduced pressure to give a brown oil. The oil was chromatographed on a 90 g KP-SIL 60 Δ Biotage column using 5% ethyl acetate in methylene chloride as the eluent. Isolation of the desired product gave 2-butyl-benzofuran-3-carboxylic acid (5-bromo-6-cyanomethoxy-naphthalen-2-ylmethyl)-methyl-amide (0.48 g, 79%) as a clear oil, MS m/z: 505 [M+H]+.

Provenance & Evidence