Triethylamine → 7-methoxy-2-(4-methoxyphenyl)-5H-pyrido[2',3':4,5]pyrrolo[2,3-b]pyridine-4-carboxamide

Participants

Reaction Steps

Dimethylformamide (0.6 mL) followed by triethylamine (47 μL, 0.34 mmol) were added to a mixture of 7-methoxy-2-(4-methoxyphenyl)-5H-pyrido[2′,3′:4,5]pyrrolo[2,3-b]pyridine-4-carboxylic acid (74 mg, 0.21 mmol), N-(3-dimethylaminopropyl)-N′-ethylcarbodimide hydrochloride (53 mg, 0.28 mmol), 1-hydroxybenzotriazole hydrate (42 mg, 0.28 mmol), and ammonium chloride (18 mg, 0.34 mmol). The reaction mixture was stirred at room temperature for 16 h. The solvent were removed under vacuum and the residue was suspended in about 10 mL of dimethylsulfoxide. The solid was collected by filtration and washed with a little dimethylsulfoxide and water. This was dried under vacuum over solid sodium hydroxide to leave 7-methoxy-2-(4-methoxyphenyl)-5H-pyrido[2′,3′:4,5]pyrrolo[2,3-b]pyridine-4-carboxamide (51 mg, 66% yield) as a yellow solid. MS (ESI) m/z 349.2 (M+H). 1H NMR (DMSO-d6) δ ppm 11.36 (1H, br. s.), 8.49 (2H, d, J=8.06 Hz), 8.26 (1H, s), 8.20 (2H, d, J=8.56 Hz), 7.86 (1H, br. s.), 7.09 (2H, d, J=8.56 Hz), 6.75 (1H, d, J=8.31 Hz), 4.00 (3H, s), 3.84 (3H, s).

Provenance & Evidence