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

Participants

Reaction Steps

A mixture of 7-methoxy-2-(4-methoxyphenyl)-5H-pyrido[3,2-b]indole-4-carboxylic acid (60 mg, 0.17 mmol), ammonium chloride (15 mg, 0.28 mmol), N-(3-dimethylaminopropyl)-N′-ethylcarbodimide hydrochloride (43 mg, 0.22 mmol), and 1-hydroxybenzotriazole hydrate (30 mg, 0.22 mmol) in a vial was flushed with nitrogen and dimethylformamide (0.5 mL) followed by triethylamine (38 μL, 0.28 mmol) were added. After stirring overnight, the reaction was diluted with methanol and the product was isolated by preparative HPLC (100×30 mm Luna C18 column, gradient elution starting with A:B=10:90 and ending with A:B=70:30 [A=10 mM NH4OAc in 5% aqueous acetonitrile; B=10 mM NH4OAc in 95% aqueous acetonitrile] over 20 min) This gave 7-methoxy-2-(4-methoxyphenyl)-5H-pyrido[3,2-b]indole-4-carboxamide (36 mg, 57% yield) as a yellow solid. MS (ESI) m/z 348.0 (M+H). 1H NMR (MeOD) δ ppm 8.27 (1H, d, J=8.85 Hz), 8.09 (1H, s), 8.04 (2H, d, J=8.85 Hz), 7.18 (1H, d, J=2.14 Hz), 7.09 (2H, d, J=8.55 Hz), 6.92 (1H, dd, J=8.55, 2.14 Hz), 3.95 (3H, s), 3.90 (3H, s).

Provenance & Evidence