反应详情

温度

100 °C

A mixture of 6-(4-fluorophenyl)-5-iodo-imidazo[2,1-b]oxazole (10.0 g, 27.4 mmol; Preparation #A.1), 2-(3-fluoro-4-nitrophenyl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane (11.9 g, 41.1 mmol; Preparation #B.1), Cs2CO3 (28.6 g, 87.8 mmol), tetrakis(triphenylphosphine)palladium(0) (3.17 g, 2.74 mmol; Strem), DME (150 mL) and water (30.0 mL) was added to a flask with screw-thread top. The flask was sealed and heated at about 100° C. for about 16 h. After cooling to ambient temperature the reaction was concentrated under reduced pressure to remove organic solvent. The resulting mixture was diluted with water (200 mL) and EtOAc (200 mL) then filtered to remove insoluble material. The layers were separated and the aqueous layer was extracted with additional EtOAc (2×200 mL). The combined organic layers were washed with brine, dried over Na2SO4, decanted, and concentrated. The crude material was purified by silica gel chromatography using DCM to give the title compound (7.80 g, 78%): LC/MS (Table 1, Method b) Rt=2.19 min; MS m/z: 342.1 (M+H)+.

1. additionwas added to a flask with screw-thread top
2. customThe flask was sealed
3. temperatureAfter cooling to ambient temperature the reaction
4. concentrationwas concentrated under reduced pressure
5. customto remove organic solvent
6. additionThe resulting mixture was diluted with water (200 mL) and EtOAc (200 mL)
7. filtrationthen filtered
8. customto remove insoluble material
9. customThe layers were separated
10. extractionthe aqueous layer was extracted with additional EtOAc (2×200 mL)
11. washThe combined organic layers were washed with brine
12. dry with materialdried over Na2SO4
13. customdecanted
14. concentrationconcentrated
15. customThe crude material was purified by silica gel chromatography