1,2-Dichlorobenzene → HCID 66605654, compound

Participants

Reaction Steps

A solution of methyl 3-azido-2-(4-(benzyloxy)phenyl)-6-(4-methoxyphenyl)isonicotinate (Example 205C, 356 mg, 0.763 mmol) in 1,2-dichlorobenzene (10 mL) was heated at 165° C. for 20 min. The solvent was removed under a stream of nitrogen to leave crude methyl 7-(benzyloxy)-2-(4-methoxyphenyl)-5H-pyrido[3,2-b]indole-4-carboxylate as a yellow solid: 1H NMR (CDCl3) δ ppm 9.37 (1H, s), 8.29 (1H, d, J=8.85 Hz), 8.13 (1H, s), 8.07-8.12 (2H, m), 7.47-7.51 (2H, m), 7.38-7.44 (2H, m), 7.31-7.37 (1H, m), 7.00-7.05 (3H, m), 5.19 (2H, s), 4.07 (3H, s), 3.88 (3H, s). This was suspended in a solution of 7 N ammonia in methanol (12 mL) and heated in a sealed microwave vial at 60° C. for 36 hr. The solvent was removed and the residue was dissolved in methylene chloride. An equal volume of hexane was added and the precipitate was collected by filtration. This gave 160 mg of 7-(benzyloxy)-2-(4-methoxyphenyl)-5H-pyrido[3,2-b]indole-4-carboxamide as a yellow solid. MS (ESI) m/z 424.1 (M+H). 1H NMR (DMSO-d6) δ ppm 11.38 (1H, s), 8.55 (1H, br. s.), 8.28 (1H, s), 8.23 (2H, d, J=8.85 Hz), 8.12 (1H, d, J=8.55 Hz), 7.83 (1H, br. s.), 7.49-7.57 (2H, m), 7.44 (2H, t, J=7.48 Hz), 7.31-7.40 (2H, m), 7.10 (2H, d, J=8.85 Hz), 6.97 (1H, dd, J=8.70, 2.29 Hz), 5.22 (2H, s), 3.85 (3H, s).

Provenance & Evidence