4-Iodoanisole → 1-(2-(4-methoxyphenyl)-1H-indol-1-yl)ethanone

Participants

Reaction Steps

The general procedure was used to convert 1-iodo-4-methoxybenzene and N-(2-ethynylphenyl)acetamide to the title product. Purification by flash chromatography gave the analytically pure product as a slightly yellow solid, 60% yield. 1H NMR (300 MHz, DMSO) δ 8.23-8.21 (d, J=8.1, 1H), 7.56-7.54 (d, J=7.5, 1H), 7.43-7.40 (d, J=8.8, 2H), 7.31-7.21 (m, 2H), 7.02-7.00 (d, J=8.8, 2H) 6.64 (s, 1H), 3.78 (s, 3H), 2.03 (s, 3H). 13C NMR (75 MHz, DMSO) δ 171.96, 160.37, 140.53, 137.75, 131.13, 129.71, 126.58, 125.29, 124.24, 121.18, 116.30, 114.97, 111.10, 56.06, 28.33. Anal. Calcd. for C17H15NO2: C, 76.96; H, 5.70; N, 5.28. Found C, 76.90; H, 5.74; N, 5.08. m.p.: 68-71° C.

Provenance & Evidence