2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → 3-(4-methoxyphenyl)-6-(morpholine-4-carbonyl)-9H-carbazole-1-carboxamide

Participants

Reaction Steps

A stirred suspension of 6-(4-methoxyphenyl)-3-(morpholine-4-carbonyl)-2,3,4,9-tetrahydro-1H-carbazole-8-carboxamide (6 mg, 0.014 mmol, Example 1) and 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (9.43 mg, 0.042 mmol) in toluene (2 mL) was heated at reflux for 2 h. The reaction mixture was concentrated, and the crude was purified by prep. HPLC to afford 3 mg of 3-(4-methoxyphenyl)-6-(morpholine-4-carbonyl)-9H-carbazole-1-carboxamide. MS (ESI) m/z 430.2 (M+H). 1H NMR (DMSO-d6) δ ppm 11.50 (s, 1H) 8.63 (s, 1H) 8.30 (s, 2H) 8.16-8.24 (m, 1H) 7.77 (d, J=8.79 Hz, 2H) 7.69 (d, J=8.35 Hz, 1H) 7.49 (br. s., 1H) 7.38-7.44 (m, 1H) 7.01 (d, J=8.79 Hz, 2H) 3.76 (s, 3H) 3.55-3.61 (m, 4H) 3.48-3.55 (m, 4H).

Provenance & Evidence