Dichloromethane → HCID 59023819, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of N-phenyl-5-bromo-1H-indazole-7-carboxamide (Example #B.1.2, 0.05 g, 0.16 mmol) and pyridine-3-yl-boronic acid (0.11 g, 0.8 mmol), 1,2-dimethoxyethane (1.3 mL), water (0.7 mL), Cs2CO3 (0.16 g, 0.48 mmol) and [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II), complex with dichloromethane (0.013 g, 0.016 mmol) was heated at about 150° C. in the microwave under an atmosphere of nitrogen for about 15 minutes. The crude product was filtered and the solvent was removed under reduced pressure. The residue was dissolved in DMSO then purified by reverse phase HPLC (Waters Symmetry C8 column (25×100 mm, 7 μm particle size) using a gradient of 10%-100% CH3CN/0.1% aqueous TFA over 8 min (10 min run time) at a flow rate of 40 mL/min) to yield N-phenyl-5-pyridin-3-yl-1H-indazole-7-carboxamide (0.014 g, 6%); (DMSO-d6, 400 MHz) δ 13.4 (bs, 1H), 10.5 (bs, 1H), 9.12 (d, 1H), 8.62 (d, 1H), 8.48 (s, 1H), 8.34 (s, 1H), 8.28 (m, 2H), 7.84 (d, 2H), 7.56 (m, 1H), 7.42 (m, 2H), 7.16 (m, 2H); RP-HPLC (Table 1, Method e) Rt=1.81 min; m/z: (M+H)+ 315.3.

Provenance & Evidence