Sodium Carbonate → tert-butyl N-[[4-[5-[3-amino-6-[2-(1-cyano-1-methyl-ethyl)-4-pyridyl]pyrazin-2-yl]-1,3,4-oxadiazol-2-yl]phenyl]methyl]-N-methyl-carbamate

Participants

Reaction Conditions

Reaction Steps

To a solution of 2-methyl-2-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-pyridyl]propane nitrile (103 mg, 0.3784 mmol) in dioxane (1.133 mL) was added of tert-butyl N-[[4-[5-(3-amino-6-bromo-pyrazin-2-yl)-1,3,4-oxadiazol-2-yl]phenyl]methyl]-N-methyl-carbamate (174.6 mg, 0.3784 mmol) and reaction was treated with 2 M aqueous solution of sodium carbonate (567.5 μL of 2 M, 1.135 mmol). The reaction mixture was degassed with 5× vacuum/nitrogen cycles. Then Pd(PPh3)4 (43.85 mg, 0.03795 mmol) was added to the reaction mixture. The reaction mixture was degassed further with 5× vacuum/nitrogen cycles and the reaction mixture was stirred in a microwave at 150° C. for 30 minutes. The reaction was diluted with ethyl acetate and aqueous sodium bicarbonate solution. The organic extracts were separated and washed with brine (×1), dried over MgSO4, filtered and concentrated in vacuo to give a black oil. Taken onto the next step without further purification (199.3 mg, assumed 100% yield).

Provenance & Evidence