Potassium Phosphate, Tribasic → HCID 86663034, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 3-chlorophenylboronic acid (73.8 mg, 0.472 mmol), methyl 2-bromo-7-formyl-5H-pyrido[3,2-b]indole-4-carboxylate (131 mg, 0.393 mmol), powdered potassium phosphate tribasic (200 mg, 0.944 mmol), dicyclohexyl(2′,6′-dimethoxybiphenyl-2-yl)phosphine (32.3 mg, 0.079 mmol), and Pd(OAc)2 (8.8 mg, 0.039 mmol) in a microwave vial was flushed with nitrogen. THF (2 mL) was added, the vial was capped and the reaction was heated in a 70° C. oil bath for 24 hr. The reaction was partitioned between EtOAc (10 mL) and water (10 mL). The precipitate was collected by filtration, washed with EtOAc and water and air dried to leave methyl 2-(3-chlorophenyl)-7-formyl-5H-pyrido[3,2-b]indole-4-carboxylate (88 mg, 0.24 mmol, 61% yield) as a yellow solid. MS (ESI) m/z 364.99 (M+H). 1H NMR (400 MHz, DMSO-d6) δ ppm 12.04 (1H, br. s.), 10.18 (1H, s), 8.47 (1H, d, J=8.06 Hz), 8.41 (1H, s), 8.28 (1H, s), 8.25 (1H, s), 8.17 (1 H, d, J=7.55 Hz), 7.83 (1H, d, J=8.06 Hz), 7.56 (1H, t, J=7.81 Hz), 7.47-7.53 (1H, m), 4.07 (3H, s).

Provenance & Evidence