反应详情

温度

70 °C

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).

1. customwas flushed with nitrogen
2. additionTHF (13 mL) was added
3. customthe vial was capped
4. customIt was partitioned between EtOAc and water
5. washThe organic phase was washed with water and brine
6. dry with materialdried with sodium sulfate
7. customthe solvent removed
8. washSilica gel chromatography (step gradient elution with DCM containing 50 to 25% hexane)