1,4-Dioxane → HCID 68079252, compound

Participants

Reaction Steps

Ethyl 1-(1,1-dimethylethyl)-3-methyl-6-{[(trifluoromethyl)sulfonyl]oxy}-1H-pyrazolo[3,4-b]pyridine-4-carboxylate (100 mg, 0.244 mmol), 3-pyridinylboronic acid (39.0 mg, 0.318 mmol), aq. saturated NaHCO3 (1 mL) and 1,4-dioxane (3 mL) were degassed with nitrogen (10 min) followed by addition of PdCl2(dppf)-CH2Cl2 adduct (9.97 mg, 0.012 mmol). The sealed mixture was irradiated (microwave) at 120° C. for 40 min. The reaction mixture was diluted with EtOAc and filtered. The filtrate was concentrated in vacuo and the crude residue was purified by silica gel chromatography (0 to 100% EtOAc/hexanes). The final product was collected as a solid, 72 mg (87%). LCMS E-S (M+H)=339.3. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.46-1.57 (m, 3H), 1.90 (s, 9H), 2.72 (s, 3H), 4.45-4.64 (m, 2H), 7.47 (dd, J=8.08, 4.80 Hz, 1H), 8.03 (s, 1H), 8.46 (dt, J=8.08, 2.02 Hz, 1H), 8.72 (dd, J=4.80, 1.52 Hz, 1H), 9.43 (d, J=1.52 Hz, 1H).

Provenance & Evidence