Tetrahydrofuran → HCID 68663647, compound

Participants

Reaction Steps

To a mixture of 3-(2-methoxy-phenyl)-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrazolo[3,4-b]pyridine (1.0 g, 2.1 mmol) and 2-amino-5-iodo-N,N-dimethylbenzamide (0.67 g, 2.3 mmol) in a 20 mL microwave reaction flask was added THF (6 mL), acetonitrile (6 mL), and 1 N aqueous sodium carbonate (6 mL, 6 mmol). The resulting suspension was degassed with nitrogen for 2 minutes. dichloro[1,1′-bis(diphenylphoshino)ferrocene]palladium(II) dichloromethane adduct (106 mg, 0.13 mmol) was added and degas was continued for another minute. The flask was capped and irradiated in a microwave reactor to 150° C. for 30 min. The reaction mixture was partitioned between aqueous saturated sodium chloride and ethyl acetate (50 mL:50 mL). The aqueous layers were extracted with ethyl acetate (30 mL×3). The combined organic phases were washed with brine, dried over sodium sulfate and evaporated. The resulting crude was purified by flash chromatography on silica gel with a gradient of ethyl acetate in hexane to afford 2-amino-N,N-dimethyl-5-[1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrazolo[3,4-b]pyridin-5-yl]-benzamide as a pale yellow solid (55%). MS: m/z 518 (M+H+).

Provenance & Evidence