Potassium Carbonate → HCID 59375045, compound

Participants

Reaction Steps

A mixture of 7-hydroxy-4-(2-methyl-3-(6-methyl-1-oxoisoindolin-2-yl)phenyl)-9H-carbazole-1-carboxamide (Example 40-2, 30 mg, 0.065 mmol) and potassium carbonate (18 mg, 0.130 mmol) in DMF (1.0 mL) was stirred at rt for 30 min, then was treated with 1-bromo-2-methoxyethane (14 mg, 0.098 mmol). The mixture was heated at 90° C. for 4 h, cooled to rt and concentrated under vacuum. The residue was purified by preparative HPLC to provide 7-(2-methoxyethoxy)-4-(2-methyl-3-(6-methyl-1-oxoisoindolin-2-yl)phenyl)-9H-carbazole-1-carboxamide as a white solid (12.5 mg, 35%). 1H NMR (400 MHz, DMSO-d6) δ 11.39 (1H, s), 8.17 (1 H, br. s.), 7.95 (1H, d, J=7.9 Hz), 7.54-7.64 (3H, m), 7.49 (3H, t, J=8.0 Hz), 7.27-7.38 (2H, m), 7.00 (1H, d, J=7.9 Hz), 6.91 (1H, d, J=8.8 Hz), 6.59 (1H, dd, J=8.8, 2.4 Hz), 4.91 (2H, d, J=3.3 Hz), 4.12 (2H, dd, J=5.5, 3.1 Hz), 3.63-3.75 (2H, m), 3.33 (3H, s), 2.44 (3H, s), 1.83 (3H, s). Mass spectrum m/z 520.1 (M+H)+.

Provenance & Evidence