Ammonia → 8-chloro-7-methoxy-2-(4-methoxyphenyl)-5H-pyrido[3,2-b]indole-4-carboxamide

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Reaction Conditions

Reaction Steps

A suspension of methyl 8-chloro-7-methoxy-2-(4-methoxyphenyl)-5H-pyrido[3,2-b]indole-4-carboxylate (29 mg, 0.073 mmol) in a 7 N solution of ammonia in MeOH (7 mL) in a sealed microwave vial was heated at 80° C. for 24 hr. The solvents were removed and preparative HPLC (100×30 mm Luna C18 column, gradient elution with A:B=30:70 to A:B=0:100 [A=10 mM NH4OAc in 5% aqueous CH3CN; B=10 mM NH4OAc in 95% aqueous CH3CN] over 20 min) afforded 8-chloro-7-methoxy-2-(4-methoxyphenyl)-5H-pyrido[3,2-b]indole-4-carboxamide (16 mg) as a yellow solid. MS (ESI) m/z 380.1 (M+H). 1H NMR (MeOD) δ ppm 8.36 (1H, s), 8.13 (1H, s), 8.06 (2H, d, J=8.85 Hz), 7.31 (1H, s), 7.10 (2H, d, J=8.85 Hz), 4.03 (3H, s), 3.90 (3H, s).

Provenance & Evidence