反应详情

温度

100 °C

To an argon purged 48 mL sealed pressure vessel was added 1,4-dioxane (2.6 mL), 4-bromo-1-trityl-1-H-pyrazole (1.00 g, 2.60 mmol), potassium fluoride (0.492 g, 8.48 mmol), 2-chloropyridine-3-boronic acid (0.808 g, 5.14 mmol), tris(dibenzylideneacetone)dipalladium (0)(0.176 g, 0.193 mmol) and tri-t-butylphosphonium tetrafluoroborate (0.168 g, 0.578 mmol). The vessel was purged with argon and heated to 100° C. for 5 hours. The mixture was cooled to RT, filtered through a pad of silica gel using EtOAc and concentrated. The crude was purified using normal phase silica gel chromatography eluting with 15-70% EtOAc/Hexanes. The product fractions were concentrated to yield 2-chloro-3-(1-trityl-1H-pyrazol-4-yl)pyridine as an off-white solid. MS m/z=422 [M+1]+. Calc'd for C27H20ClN3: 421.92.

1. customTo an argon purged 48 mL
2. customsealed pressure vessel
3. customThe vessel was purged with argon
4. temperatureThe mixture was cooled to RT
5. filtrationfiltered through a pad of silica gel
6. concentrationconcentrated
7. customThe crude was purified
8. washeluting with 15-70% EtOAc/Hexanes
9. concentrationThe product fractions were concentrated