Acetic Acid → HCID 67995329, compound

Participants

Reaction Steps

To a light burgundy, homogeneous solution of 7-amino-4-(3-(6-chloro-1-oxoisoindolin-2-yl)-2-methylphenyl)-9H-pyrido[3,4-b]indole-1-carboxamide (0.0695 g, 0.144 mmol), dihydrofuran-3(2H)-one (0.050 g, 0.577 mmol) and acetic acid (0.041 mL, 0.721 mmol) in dichloromethane (1.602 mL) and THF (1.602 mL) was added sodium triacetoxyborohydride (0.122 g, 0.577 mmol). The reaction was stirred overnight. Water (2 mL) was added, and the solution was stirred at room temperature for 10 min. EtOAc (50 mL) and water (20 mL) were added. After separation of layers, the organic layer was washed with sat. aq. NaHCO3, brine (20 mL), dried over MgSO4, and concentrated in vacuo to give a residue which was diluted with DMSO (0.2 mL) and MeOH (0.8 mL) and purified by reverse phase HPLC. The appropriate fractions were collected, basified with NaHCO3 (solid), and concentrated in vacuo. The residue was extracted with CH2Cl2 (3×). The combined extract was dried over Na2SO4 and concentrated in vacuo to give the desired product (0.00234 g, 4.03 μmol, 2.79% yield) as a tan solid. LC/MS (M+H)=552.24.

Provenance & Evidence