Acetic Acid → 2-((3-(1-Carbamoyl-7-(2-methoxyethoxy)-9H-pyrido[3,4-b]indol-4-yl)-2-fluorophenylamino)methyl)-5-methylbenzoic acid

Participants

Reaction Steps

To a light orange, homogeneous solution of 4-(3-amino-2-fluorophenyl)-7-(2-methoxyethoxy)-9H-pyrido[3,4-b]indole-1-carboxamide (0.0767 g, 0.194 mmol), 2-formyl-5-methylbenzoic acid (0.096 g, 0.583 mmol) and acetic acid (0.033 mL, 0.583 mmol) in dichloromethane (3.89 mL) and THF (2.59 mL) under nitrogen was added sodium triacetoxyborohydride (0.206 g, 0.972 mmol). The reaction was stirred overnight. More sodium triacetoxyborohydride (0.206 g, 0.972 mmol) and acetic acid (0.033 mL, 0.583 mmol) were added. After 4.5 hr, water (3 mL) was added, and the reaction was stirred for 10 min. EtOAc (50 mL) and water (20 mL) were added, and the layers were separated. The organic layer was washed with water (6×20 mL) and brine (20 mL), dried over MgSO4, and concentrated in vacuo to give a crude product used in subsequent step.

Provenance & Evidence