2-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenyl → 1-methyl-4-(2-(phenylamino)quinolin-8-yl)-1H-pyrrole-2-carboxamide

Participants

Reaction Conditions

Reaction Steps

A mixture of 4-bromo-1-methyl-1H-pyrrole-2-carboxamide (164a; 40 mg, 0.20 mmol), (2-(phenylamino)quinolin-8-yl)boronic acid (Example 165d; 68 mg, 0.26 mmol), XPhos (10 mg) and Pd2(dba)3 (10 mg) in 2 mL of dioxane and 0.5 mL of 2 N Na2CO3 was heated in a microwave at 130° C. for 20 min. The mixture was partitioned between 20 mL of EtOAc and 5 mL of 0.5 N NaOH. The organic layer was concentrated, and purified on silica gel column (25-85% EtOAc in hexanes) to give 1-methyl-4-(2-(phenylamino)quinolin-8-yl)-1H-pyrrole-2-carboxamide (19 mg, 27% yield) as an off-white crystalline solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 9.35 (1H, s), 8.06 (1H, d, J=8.8 Hz), 7.90 (2H, m), 7.84 (1H, d, J=1.8 Hz), 7.68 (1H, dd, J=7.3, 1.5 Hz), 7.56 (1H, dd, J=7.8, 1.4 Hz), 7.48 (1H, br.), 7.37 (1H, d, J=2.0 Hz), 7.35-7.24 (3H, m), 7.06 (1H, d, J=8.8 Hz), 7.00 (1H, t, J=7.3 Hz), 6.82 (1H, br.), 3.87 (3H, s). m/z (ESI, +ve) 343.1 (M+H)+.

Provenance & Evidence