Methanol → HCID 59375119, compound

Participants

Reaction Steps

A solution of 4-(2-fluoro-3-methoxyphenyl)-7-(4-methylpiperazine-1-carbonyl)-9H-carbazole-1-carboxamide (Example 3-137, 3.6 g, 7.82 mmol) in DCM (42 mL) was stirred at 0° C. and treated with boron tribromide (1 M in DCM, 94 mL, 94 mmol) and the mixture was stirred at rt overnight. The mixture was cooled again to 0° C. and treated slowly with methanol. The mixture was concentrated and purified by column chromatography on neutral alumina (eluting with 90:10 EtOAc-methanol) to provide 4-(2-fluoro-3-hydroxyphenyl)-7-(4-methylpiperazine-1-carbonyl)-9H-carbazole-1-carboxamide as a light colored solid (2.0 g, 57%). 1H NMR (400 MHz, DMSO-d6) δ 11.75 (s, 1H), 10.08 (s, 1H), 8.25 (br. s., 1H), 8.05 (d, J=7.6 Hz, 1H), 7.81 (s, 1H), 7.59 (br. s., 1H), 7.17 (m, 3H), 7.11 (d, J=7.6 Hz, 1H), 6.99 (dd, J=8.0, 1.2 Hz, 1H), 6.91 (t, J=7.2 Hz, 1H), 3.51 (br. s., 2H), 3.34 (m, 5H), 2.34 (br. s., 4H). Mass spectrum m/z 447.0 (M+H)+.

Provenance & Evidence