反应详情

温度

100 °C

A suspension of 6-((6-chloro-[1,2,4]triazolo[4,3-b]pyridazin-3-yl)methyl)quinoline (170 mg, 575 μmol), (2-chloro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)methanol (309 mg, 1150 μmol), dichloro[1,1′bis(diphenylphoshino)ferrocene]palladium(ii)dichloromethane adduct (126 mg, 172 μmol), cesium carbonate (749 mg, 2299 μmol) in Dioxane (0.3 mL) and water (0.3 mL) was sparged with argon for 5 min then heated to 100° C. with stirring. 1:30 am. After 90 min, LCMS suggests 95% conversion. Reaction then partitioned between 9:1 CHCl3/IPA (25 mL) and 5% NaHCO3 (15 mL). Aqueous further extracted with 9:1 CHCl3/IPA (2×10 mL). Combined organics dried with MgSO4, concentrated onto dry silica (10 g), and then purified on silica (12 g) eluting with 0>10% 2M NH3 in MeOH/DCM. Resulting solid triturated with methanol (2 mL) and collected by filtration. MS (ESI pos. ion) m/z: 402 (MH+). Calc'd exact mass for C22H16ClN5O: 401.

1. customwas sparged with argon for 5 min
2. customReaction
3. customthen partitioned between 9:1 CHCl3/IPA (25 mL) and 5% NaHCO3 (15 mL)
4. extractionAqueous further extracted with 9:1 CHCl3/IPA (2×10 mL)
5. dry with materialCombined organics dried with MgSO4
6. concentrationconcentrated onto dry silica (10 g)
7. custompurified on silica (12 g)
8. washeluting with 0>10% 2M NH3 in MeOH/DCM
9. customResulting solid
10. customtriturated with methanol (2 mL)
11. filtrationcollected by filtration