Water → HCID 19870652, compound

Participants

Reaction Steps

A mixture of N-cyclopentylmethyl-3-formylindole-6-acetamide (0.52 g), t-butyl 4-bromomethyl-3-methoxybenzoate (0.66 g), and potassium carbonate (0.37 g) in N,N-dimethylformamide (10 ml) was stirred for 48 hr under a nitrogen atmosphere. Water was added to give a precipitate which was collected by filtration and purified by flash chromatography, eluting with 1:49 methanol:chloroform, to give t-butyl 4-[6-(cyclopentylmethylcarbamoyl)methyl-3-formylindol-1-ylmethyl]-3-methoxybenzoate (0.90 g, 97%) as a white solid; partial NMR (80 MHz, CDCl3): 1.56 (s, 9H, C(CH3)3), 3.09(t, 2H, NHCH2), 3.65(s, 2H, COCH2), 3.93(s, 3H, OCH3), 9.98(s, 1H, CHO).

Provenance & Evidence