Ethyl Acetate → N-[(4,6-Dimethyl-2-oxo-1,2-dihydro-3-pyridinyl)methyl]-6-{4-[(methylamino)sulfonyl]phenyl}-1-(1-methylethyl)-1H-indazole-4-carboxamide

Participants

Reaction Conditions

Reaction Steps

In a 25 mL sealable tube under nitrogen were combined 6-bromo-N-[(4,6-dimethyl-2-oxo-1,2-dihydro-3-pyridinyl)methyl]-1-(1-methylethyl)-1H-indazole-4-carboxamide (100 mg, 0.24 mmol), {4-[(methylamino)sulfonyl]phenyl}boronic acid (77 mg, 0.36 mmol) in DME/water (3 mL:1 mL). PdCl2(dppf)-CH2Cl2 (9.8 mg, 0.012 mmol) was added and the resulting mixture was degassed with nitrogen for 10 min. Sodium bicarbonate (60.4 mg, 0.72 mmol) was added, the vessel was sealed, and the insoluble mixture was heated in a microwave at 140° C. for 30 min. EtOAc was added and the solution was filtered thru Celite and evaporated. DCM/MeOH (1:1) was added, it was pre-absorbed on silica gel and purified by SiO2 chromatography (eluent: gradient 100% DCM to 90:10:1 DCM/MeOH/NH4OH). Fractions were evaporated. EtOAc was added along with some hexanes, it was sonicated and the solids that precipitated were filtered, washed with DCM and dried to afford the title compound (67 mg, 54%) as a beige solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 11.54 (s, 1H) 9.87 (br. s., 1H) 8.62 (t, J=4.80 Hz, 1H) 8.37 (s, 1H) 8.07 (s, 1H) 7.82-7.86 (m, 3H) 7.35 (s, 1H) 7.32 (s, 1H) 5.89 (s, 1H) 5.15 (quin, J=6.63 Hz, 1H) 4.39 (d, J=4.80 Hz, 2H) 3.04 (s, 3H) 2.22 (s, 3H) 2.12 (s, 3H) 1.51 (s, 3H) 1.49 (s, 3H). MS (ES) [M+H]+ 507.9.

Provenance & Evidence