Potassium Phosphate, Tribasic → HCID 66604014, compound

Participants

Reaction Conditions

Reaction Steps

A flask containing a mixture of phenylboronic acid (0.889 g, 7.29 mmol), methyl 9-(benzyloxy)-2-bromo-5H-pyrido[3,2-b]indole-4-carboxylate (1.50 g, 3.65 mmol), powdered potassium phosphate tribasic (2.48 g, 11 7 mmol), 2-dicyclohexylphosphino-2′,4′,6′-tri-iso-propyl-1,1′-biphenyl (0.348 g, 0.729 mmol), and Pd(OAc)2 (0.082 g, 0.365 mmol) was flushed with nitrogen. THF (12 mL) was added and the mixture was heated at 80° C. for 2 hr. The reaction was diluted with EtOAc, washed with water, sat. aq. Na2CO3 solution, brine, and dried with sodium sulfate. The solvent was removed and the residue was suspended in a little EtOAc. Filtration and washing with EtOAc, afforded methyl 9-(benzyloxy)-2-phenyl-5H-pyrido[3,2-b]indole-4-carboxylate (1.47 g, 3.42 mmol, 94%). MS (ESI) m/z 408.9 (M+H). 1H NMR (500 MHz, DMSO-d6) δ ppm 11.68 (1H, s), 8.33 (1H, s), 8.28 (2H, d, J=7.32 Hz), 7.87 (2H, d J=7.63 Hz), 7.37-7.57 (8H, m), 6.99 (1H, d, J=8.24 Hz), 5.45 (2H, s), 4.09 (3H, s).

Provenance & Evidence