Sodium Carbonate → tert-Butyl {(1R,2R)-2-[({4-[6-(difluoromethoxy)pyrazolo[1,5-a]pyrimidin-3-yl]-5-ethylthiophen-2-yl}carbonyl)amino]-3,3-difluorocyclohexyl}carbamate

Participants

Reaction Conditions

Reaction Steps

3-Bromo-6-(difluoromethoxy)pyrazolo[1,5-a]pyrimidine (0.030 g, 0.114 mmol), tert-butyl[(1R,2R)-2-({[5-ethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)thiophen-2-yl]carbonyl}amino)-3,3-difluorocyclohexyl]carbamate (0.059 g, 0.115 mmol), Pd(PPh3)4 (6.57 mg, 0.007 mmol), and 2 M Na2CO3 (aq) (0.170 mL, 0.341 mmol) were placed in a sealed tube and DMF (1.14 mL) added. The mixture was purged with N2 for 5 min. The reaction was heated to 85° C. for 16 h. The mixture was cooled to room temperature, diluted with dichloromethane, and washed twice with saturated sodium bicarbonate (aq) and once with brine. The organic layer was dried with sodium sulfate, filtered, and concentrated under reduced pressure. The crude product was purified by column chromatography (0-70% EtOAc/Hex) to give the title compound (0.037 g, 0.064 mmol). LRMS (APCI) calc'd for (C25H29F4N5O4S) [M+H]+, 572.2; found 572.1.

Provenance & Evidence