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

Participants

Reaction Conditions

Reaction Steps

A mixture of phenylboronic acid (41.9 mg, 0.343 mmol),methyl 2-bromo-7-(morpholinosulfonyl)-5H-pyrido[3,2-b]indole-4-carboxylate (120 mg, 0.264 mmol), potassium phosphate tribasic (146 mg, 0.687 mmol), dicyclohexyl(2′,6′-dimethoxybiphenyl-2-yl)phosphine (22 mg, 0.053 mmol), and Pd(OAc)2 (5.9 mg, 0.026 mmol) in a microwave vial was flushed with nitrogen. THF (1.3 mL) was added, the vial was capped and the reaction was heated in a 70° C. for 18 hr. It was partitioned between EtOAc and water and the organic phase was separated and washed with brine. It was dried with sodium sulfate and the solvent were removed. The residue was dissolved in DCM and radial chromatography (step gradient elution with DCM containing 0 to 10% EtOAc) afforded methyl 7-(morpholinosulfonyl)-2-phenyl-5H-pyrido[3,2-b]indole-4-carboxylate (107 mg, 0.237 mmol, 90% yield) as a yellow solid. MS (ESI) m/z 450.0 (M−H). 1H NMR (500 MHz, DMSO-d6) d ppm 12.04 (1H, s), 8.58 (1H, d, J=8.24 Hz), 8.47 (1H, s), 8.26 (2H, d, J=7.32 Hz), 8.19 (1H, d, J=1.22 Hz), 7.67 (1H, dd, J=8.24, 1.53 Hz), 7.58 (2H, t, J=7.63 Hz), 7.46-7.52 (1H, m), 4.11 (3H, s), 3.62-3.72 (4H, m), 2.92-3.00 (4H, m).

Provenance & Evidence