反应详情

温度

80 °C

1,1′-bis(diphenylphosphino)ferrocene-palladium(II)dichloride dichlormethane complex (17.1 mg, 0.021 mmol) was added to a stirred suspension of [(3R,3aR,6R,6aS)-3-(1-allyl-6-chloro-5-iodo-imidazo[4,5-b]pyridin-2-yl)oxy-2,3,3a,5,6,6a-hexahydrofuro[3,2-b]furan-6-yl]oxy-tert-butyl-dimethyl-silane (99.8 mg, 0.173 mmol), 1-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)pyrrolidine (59.6 mg, 0.218 mmol), and tripotassium phosphate (225.0 mg, 1.060 mmol) in dioxane (1.38 ml) and water (0.35 ml). The reaction mixture was degassed (3×) and placed under nitrogen before being heated to 80° C. After 15 hours, the reaction mixture was cooled to room temperature. The reaction mixture was partitioned between EtOAc (40 ml) and water (40 ml). The aqueous layer was extracted with EtOAc (2×20 ml). The organic layers were combined, washed with brine, dried over MgSO4, filtered, and evaporated under reduced pressure to give an amber residue. This residue was dissolved in DCM, loaded onto a 5 g silica solid load cartridge and purified using an ISCO Rf and a 4 g silica column (CV=4.8 ml). The column was eluted as follows: 100% hexane (5 CV), 0-30% EtOAc/hexane gradient (70 CV), 30% EtOAc/hexane (21 CV) at 18 ml/min. The product fractions were combined and evaporated under reduced pressure to give the title compound as a yellow residue. LC-MS: calculated for C31H41ClN4O4Si 596.26 observed m/e: 597.39 (M+H)+ (Rt 1.34/2 min).

1. customThe reaction mixture was degassed (3×)
2. temperaturethe reaction mixture was cooled to room temperature
3. customThe reaction mixture was partitioned between EtOAc (40 ml) and water (40 ml)
4. extractionThe aqueous layer was extracted with EtOAc (2×20 ml)
5. washwashed with brine
6. dry with materialdried over MgSO4
7. filtrationfiltered
8. customevaporated under reduced pressure
9. customto give an amber residue
10. custompurified
11. washThe column was eluted
12. customevaporated under reduced pressure