Dichloromethane → HCID 178492096, compound

Participants

Reaction Steps

2,2-Dimethyl-propionic acid 5-bromo-3-(3-methoxy-pyridin-2-yl)-pyrazolo[3,4-b]pyridin-1-ylmethyl ester (570 mg, 1.36 mmol), 2-amino-N,N-dimethyl-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzamide (570 mg, 1.96 mmol), [1,1′-bis(diphenylphosphino)-ferrocene]dichloropalladium(II) complex in dichloromethane (1:1, 111 mg, 0.136 mmol), tetrahydrofuran (3 ml), acetonitrile (6 ml), water (3 ml), and saturated sodium bicarbonate (3 ml) were combined and irradiated in a microwave reactor for 20 minutes at 120° C. Water was added to the reaction mixture, and this was extracted with dichloromethane. The organic layer was dried over sodium sulfate and concentrated. The crude product was purified by flash chromatography (0-100% [10% methanol in ethyl acetate] in hexanes) to give 205 mg (31%) 2-amino-5-[3-(3-methoxy-pyridin-2-yl)-1H-pyrazolo[3,4-b]pyridin-5-yl]-N,N-dimethyl-benzamide. MS: m/z 503.4 (M+H+).

Provenance & Evidence