Potassium Phosphate, Tribasic → HCID 66604850, compound

Participants

Reaction Conditions

Reaction Steps

A flask containing a mixture of 1-methyl-1H-indazol-5-ylboronic acid (590 mg, 3.35 mmol), methyl 2-bromo-7-chloro-5-(4-methoxybenzyl)-5H-pyrido[3,2-b]indole-4-carboxylate (1.19 g, 2.58 mmol), powdered potassium phosphate tribasic (1.31 g, 6.19 mmol), dicyclohexyl(2′,6′-dimethoxybiphenyl-2-yl)phosphine (0.212 g, 0.516 mmol), and Pd(OAc)2 (0.058 g, 0.258 mmol) was flushed with nitrogen. THF (10 mL) was added and the reaction was heated at 70° C. for 15 hr. The reaction 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-(1-methyl-1H-indazol-5-yl)-5H-pyrido[3,2-b]indole-4-carboxylate (720 mg, 1.41 mmol, 55% yield) as a solid. MS (ESI) m/z 511.14 (M+H). 1H NMR (500 MHz, chloroform-d) δ ppm 8.47 (1H, s), 8.42 (1H, d, J=8.24 Hz), 8.27 (1H, dd, J=8.55, 1.53 Hz), 8.07 (2H, d, J=2.14 Hz), 7.50 (1H, d, J=8.55 Hz), 7.46 (1H, s), 7.35 (1H, dd, J=8.24, 1.53 Hz), 6.86-6.91 (2H, m), 6.76 (2H, d, J=8.85 Hz), 5.67 (2H, s), 4.12 (3H, s), 3.82 (3H, s), 3.73 (3H, s).

Provenance & Evidence