Dichloromethane → HCID 178434367, compound

Participants

Reaction Steps

In a microwave vial was charged with tert-butyl 5-bromo-3-methyl-1H-pyrazolo[3,4-c]pyridine-1-carboxylate (53 mg, 0.17 mmol), 1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (70.6 mg, 0.34 mmol), potassium acetate (205.5 mg, 2.09 mmol), cesium carbonate (166.0 mg, 0.51 mmol), and bis(diphenylphosphino)ferrocene]dichloropalladium (II), complexed with dichloromethane (1:1) (13.9 mg, 0.017 mmol). DMF (2.6 mL) and water (0.5 mL) were added. Nitrogen was passed through the mixture for 15 minutes and the vial was capped. The reaction mixture was subjected to microwave irradiation at 125° C. for 20 min. The reaction mixture was filtered through a pad of Celite® and diluted with water and EtOAc. The organic layer was washed with brine, dried over Na2SO4, filtered, and evaporated in vacuo. The crude product was purified using flash chromatography (Si-PPC gradient elution, solvent: 50-100% ethyl acetate in heptanes, followed by 0-30% methanol in ethyl acetate) to give 127 as a foam (26.0 mg, 71.8%). 1H NMR (400 MHz, DMSO) δ 13.08 (broad s, 1H), 8.90 (s, 1H), 8.19 (s, 1H), 7.98 (s, 1H), 7.94 (s, 1H), 3.88 (s, 3H), 2.53 (s, 3H). LC/MS: m/z 214.1 [M+1]

Provenance & Evidence