Potassium Phosphate, Tribasic → methyl 7-(benzyloxy)-2-(3-(trifluoromethyl)phenyl)-5H-pyrido[3,2-b]indole-4-carboxylate

Participants

Reaction Conditions

Reaction Steps

A mixture of 3-(trifluoromethyl)phenylboronic acid (0.59 g, 3.1 mmol), methyl 7-(benzyloxy)-2-bromo-5H-pyrido[3,2-b]indole-4-carboxylate (1.07 g, 2.60 mmol), powdered potassium phosphate tribasic (1.33 g, 6.24 mmol), dicyclohexyl(2′,6′-dimethoxybiphenyl-2-yl)phosphine (0.214 g, 0.520 mmol), and Pd(OAc)2 (0.058 g, 0.260 mmol) in a microwave vial was flushed with nitrogen. THF (13 mL) was added, the vial was capped, and the reaction was heated in a 70° C. oil bath for 24 hr. It was partitioned between EtOAc and water. The organic phase was washed with water and brine, dried with sodium sulfate, and the solvent removed. Silica gel chromatography (step gradient elution with DCM containing 50 to 25% hexane) afforded methyl 7-(benzyloxy)-2-(3-(trifluoromethyl)phenyl)-5H-pyrido[3,2-b]indole-4-carboxylate (1.03 g, 2.16 mmol, 83% yield) as a tan solid. MS (ESI) m/z 477.1 (M+H). 1H NMR (500 MHz, chloroform-d) δ ppm 9.47 (1H, s), 8.44 (1H, s), 8.30-8.37 (2H, m), 8.21 (1H, s), 7.57-7.67 (2H, m), 7.49 (2H, d, J=7.32 Hz), 7.42 (2H, t, J=7.48 Hz), 7.32-7.38 (1H, m), 7.03-7.09 (2H, m), 5.21 (2H, s), 4.10 (3H, s).

Provenance & Evidence