Potassium Phosphate, Tribasic → methyl 2-(3-chlorophenyl)-7-(4-morpholinyl)-5H-pyrido[2',3':4,5]pyrrolo[2,3-b]pyridine-4-carboxylate

Participants

Reaction Conditions

Reaction Steps

A mixture of 3-chlorophenylboronic acid (48.0 mg, 0.307 mmol), methyl 2-bromo-7-(4-morpholinyl)-5H-pyrido[2′,3′:4,5]pyrrolo[2,3-b]pyridine-4-carboxylate (100 mg, 0.256 mmol), finely powdered potassium phosphate tribasic (130 mg, 0.613 mmol), dicyclohexyl(2′,6′-dimethoxybiphenyl-2-yl)phosphine (21 mg, 0.051 mmol), and Pd(OAc)2 (5.7 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. oil bath for 24 hr. After cooling, it was partitioned between EtOAc and water. The organic phase was extracted with brine and dried with sodium sulfate. The solvents were removed and radial chromatography (step gradient elution with DCM containing 0 to 50% EtOAc) afforded methyl 2-(3-chlorophenyl)-7-(4-morpholinyl)-5H-pyrido[2′,3′:4,5]pyrrolo[2,3-b]pyridine-4-carboxylate (55 mg, 0.130 mmol, 51% yield). MS (ESI) m/z 423.11 (M+H). 1H NMR (500 MHz, chloroform-d) δ ppm 9.51 (1H, s), 8.43 (1H, d, J=8.55 Hz), 8.16 (1H, t, J=1.83 Hz), 8.13 (1H, s), 7.99 (1H, d, J=7.93 Hz), 7.42 (1H, t, J=7.78 Hz), 7.33-7.38 (1H, m), 6.67 (1H, d, J=8.85 Hz), 4.08 (3H, s), 3.84-3.91 (4H, m), 3.67-3.75 (4H, m).

Provenance & Evidence