Triethylamine → 1-(4-fluorophenyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazolo[3,4-b]pyridine

Participants

Reaction Conditions

Reaction Steps

A vial was charged with bis(acetonitrile)palladium(II) chloride (1.038 mg, 4.00 μmol), dicyclohexyl(2′,6′-dimethoxybiphenyl-2-yl)phosphine (3.28 mg, 8.00 μmol), and Intermediate 2A (0.068 g, 0.200 mmol). The vial was capped with a rubber septum and then evacuated and backfilled with N2 (this sequence was carried out a total of 2 times). Dioxane (0.120 mL) was added via syringe, through the septum, followed by the addition of triethylamine (0.084 mL, 0.600 mmol) and 4,4,5,5-tetramethyl-1,3,2-dioxaborolane (0.044 mL, 0.300 mmol) dropwise. The septum was then replaced with a Teflon screw valve, and the vial sealed. The reaction mixture was heated at 110° C. After 14 h, the reaction mixture was allowed to cool to room temperature. The reaction mixture was filtered through a disposable fritted funnel and the filter cake washed with CH2Cl2. The filtrate was concentrated to afford the title compound as a yellow solid. Intermediate 105B: MS (ESI): m/z=340.2 [M+H]+ HPLC Peak ret. T=2.00 minutes was product. (HPLC conditions: Column:Luna C18 4.6×30 mm 3 u A:10:90 H2O:ACN NH4OAc/B:10:90 H2O:ACN NH4OAc; 0%-95% B in 2 min; 4 mL/min flow).

Provenance & Evidence