Potassium Phosphate, Tribasic → HCID 66605177, compound

Participants

Reaction Conditions

Reaction Steps

A flask containing a mixture of 6-methylpyridin-3-ylboronic acid (0.592 g, 4.32 mmol), methyl 2-bromo-7-chloro-5-(4-methoxybenzyl)-5H-pyrido[3,2-b]indole-4-carboxylate (1.24 g, 2.70 mmol), powdered potassium phosphate tribasic (1.38 g, 6.48 mmol), dicyclohexyl(2′,6′-dimethoxybiphenyl-2-yl)phosphine (0.222 g, 0.540 mmol), and Pd(OAc)2 (0.061 g, 0.270 mmol) was flushed with nitrogen. THF (10 mL) was added and the reaction was heated at 70° C. for 15 hr. This was partitioned between EtOAc and water. The organic phase was washed with water and brine, dried with sodium sulfate, and the solvent was removed. Silica gel chromatography (step gradient elution with DCM containing 0 to 3% EtOAc) afforded methyl 7-chloro-5-(4-methoxybenzyl)-2-(6-methylpyridin-3-yl)-5H-pyrido[3,2-b]indole-4-carboxylate (360 mg, 0.763 mmol, 28% yield) as a solid. MS (ESI) m/z 472.12 (M+H). 1H NMR (500 MHz, chloroform-d) δ ppm 9.18 (1H, s), 8.33-8.42 (2H, m), 7.98 (1H, s), 7.47 (1H, s), 7.34 (1H, d, J=8.24 Hz), 7.28 (1H, d, J=7.93 Hz), 6.86 (2H, d, J=8.24 Hz), 6.75 (2H, d, J=8.55 Hz), 5.66 (2H, s), 3.78-3.84 (3H, m), 3.69-3.74 (3H, m), 2.63 (3H, s).

Provenance & Evidence