Methanol → HCID 66605825, compound

Participants

Reaction Conditions

Reaction Steps

A solution of isopropyl 4-carbamoyl-2-phenyl-5H-pyrido[3,2-b]indole-7-carboxylate (2 g, 5.36 mmol) in a mixture of THF (36 ml), MeOH (15 ml) and 1 N aqueous NaOH (12 ml, 120 mmol) was stirred at 25° C. overnight. The organic solvents were removed and the residue was dissolved in water, washed with DCM (20 mL), and acidified to about pH 3 with 1 N aqueous HCl to give a yellow gel-like precipitate. This was chilled in an ice bath and the precipitate was collected by filtration, washed with water, and dried to leave 4-carbamoyl-2-phenyl-5H-pyrido[3,2-b]indole-7-carboxylic acid (2.1 g, 5.1 mmol, 95% yield). MS (ESI) m/z 332.00 (M+H). 1H NMR (500 MHz, MeOD) δ ppm 8.67 (1H, d, J=8.55 Hz), 8.58-8.64 (1H, m), 8.54 (1H, s), 8.03-8.17 (3H, m), 7.67-7.79 (3H, m).

Provenance & Evidence