Potassium Phosphate, Tribasic → HCID 66606265, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 3-chlorophenylboronic acid (34 mg, 0.22 mmol), methyl 2-bromo-7-(morpholinomethyl)-5H-pyrido[3,2-b]indole-4-carboxylate (75 mg, 0.19 mmol), powdered potassium phosphate tribasic (95 mg, 0.45 mmol), dicyclohexyl(2′,6′-dimethoxybiphenyl-2-yl)phosphine (15 mg, 0.037 mmol), and Pd(OAc)2 (4.2 mg, 0.019 mmol) in a microwave vial was flushed with nitrogen. THF (928 μL) 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 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 2% MeOH) afforded methyl 2-(3-chlorophenyl)-7-(morpholinomethyl)-5H-pyrido[3,2-b]indole-4-carboxylate (59 mg, 0.14 mmol, 73% yield) as a yellow oil. MS (ESI) m/z 435.9 (M+H). 1H NMR (400 MHz, chloroform-d) δ ppm 9.54 (1H, s), 8.40 (1H, d, J=8.06 Hz), 8.26 (1H, s), 8.23 (1H, t, J=1.76 Hz), 8.06 (1H, dt, J=7.74, 1.42 Hz), 7.56 (1H, s), 7.46 (1H, t, J=7.68 Hz), 7.33-7.43 (2H, m), 4.13 (3H, s), 3.75-3.80 (4H, m), 3.73 (2H, s), 2.51-2.58 (4H, m).

Provenance & Evidence