Ammonia methanol → 2-bromo-7-(morpholine-4-carbonyl)-5H-pyrido[3,2-b]indole-4-carboxamide

Participants

Reaction Conditions

Reaction Steps

Methyl 2-bromo-7-(morpholine-4-carbonyl)-5H-pyrido[3,2-b]indole-4-carboxylate (1.008 g, 2.410 mmol, Example 212D) was suspended in NH3/MeOH (7M) (18 mL, 126 mmol) in a sealed microwave vial. The mixture was heated at 105° C. for 8 hours in a microwave reactor. Product crystallized from reaction mixture upon cooling and was collected by filtration, washed with MeOH and dried in nitrogen stream to give 736.4 mg 2-bromo-7-(morpholine-4-carbonyl)-5H-pyrido[3,2-b]indole-4-carboxamide. 1H NMR (DMSO-d6) δ ppm 11.4 (b, 1H), 8.56 (s, 1H), 8.22 (d, 1H, J=8.6), 7.81 (s, 1H), 7.31 (dd, 1H, J=7.9, 1.2), 3.75-3.35 (b, 10H). MS (ESI) m/e−=401/403, m/e+=403/405 (1 Br isotope pattern) consistent with [M−H]− and [M+H]+. HPLC retention time 6.74 min. (Sunfire C18 3.5 μm, 4.6×150 mm column, 15 min gradient, 10-100% B, 1 mL/min. Solvent A: 5% CH3CN—95% H2O—0.1% TFA; Solvent B: 95% CH3CN—5% H2O—0.1% TFA).

Provenance & Evidence