Sodium Carbonate → HCID 178446749, compound

Participants

Reaction Conditions

Reaction Steps

4-iodo-3-methyl-1H-pyrazolo[3,4-b]pyridine (150 mg, 0.5790 mmol), tert-butyl 2-methyl-2-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)butylcarbamate (225.4 mg, 0.5790 mmol), Na2CO3 (868.5 μL of 2 M, 1.737 mmol) and Pd(PPh3)4 (66.91 mg, 0.05790 mmol) were placed in a microwave tube and Dioxane (1.500 mL) was added. The resulting suspension was stirred at 150° C. in the microwave (using a 10 minute ramp and nitrogen cooling) for 45 minutes. The reaction mixture was partitioned between EtOAc and brine. The aqueous layer was extracted with EtOAc (3×20 mL) and the combined organics were dried over Na2SO4, filtered and concentrated under reduced pressure to give a yellow gum. The mixture was purified by column chromatography (75% EtOAc in hexanes, ˜75 mL silica) to give a slightly yellow gum (203 mg, 89% Yield).

Provenance & Evidence