Potassium Phosphate, Tribasic → HCID 66604957, compound

Participants

Reaction Conditions

Reaction Steps

A flask containing a mixture of 3-fluoro-4-methoxyphenylboronic acid (0.901 g, 5.30 mmol), methyl 2-bromo-7-chloro-5H-pyrido[3,2-b]indole-4-carboxylate (1.5 g, 4.4 mmol), powdered potassium phosphate tribasic (2.25 g, 10 6 mmol), dicyclohexyl(2′,6′-dimethoxybiphenyl-2-yl)phosphine (0.363 g, 0.883 mmol), and Pd(OAc)2 (0.099 g, 0.44 mmol) was flushed with nitrogen, THF (22 mL) was added, and the reaction was heated at 70° C. for 20 hr. This was partitioned between EtOAc and water and the organic phase was washed with water and brine and then dried with sodium sulfate. Removal of the solvent followed by silica gel chromatography (step gradient elution with DCM containing 75 to 0% hexane) afforded methyl 7-chloro-2-(3-fluoro-4-methoxyphenyl)-5H-pyrido[3,2-b]indole-4-carboxylate (1.29 g, 3.35 mmol, 76% yield) as a light green solid. MS (ESI) m/z 385.13 (M+H). 1H NMR (500 MHz, DMSO-d6) δ ppm 11.89 (1H, s), 8.19 (1H, d, J=8.24 Hz), 7.92 (1H, s), 7.76 (1H, d, J=1.53 Hz), 7.35 (1H, dd, J=8.55, 1.83 Hz), 4.04 (3H, s).

Provenance & Evidence