反应详情

温度

50 °C

To a solution of 2.0 g of tert-butyl 3-bromo-5-cyano-1H-1-indazolecarboxylate in 30 ml tetrahydrofuran were added 70 mg of palladium(II) acetate, 218 mg of 2-(dicyclohexylphosphino)biphenyl, 1.19 g of potassium fluoride and 1.30 g of 4-fluorophenylboronic acid, and the mixture was stirred at 50° C. for one day. After removing the solvent by distillation, the residue was diluted with 40 ml of ethyl acetate. The mixture was sequentially washed with water and brine, dried over anhydrous magnesium sulfate and the solvent was evaporated. The residue was dissolved in 25 ml of methylene chloride, and 5 ml of trifluoroacetic acid was added, followed by stirring at room temperature for 1 hour. After removing the solvent by distillation, the residue was diluted with 40 ml of ethyl acetate. The mixture was sequentially washed with saturated aqueous sodium hydrogencarbonate solution and brine, dried over anhydrous magnesium sulfate and the solvent was evaporated. The crude product was purified and separated by silica gel column chromatography (ethyl acetate:toluene=1:19 to 1:9), to give 1.09 g of the title compound as bright yellow crystals.

1. customAfter removing the solvent
2. distillationby distillation
3. additionthe residue was diluted with 40 ml of ethyl acetate
4. washThe mixture was sequentially washed with water and brine
5. dry with materialdried over anhydrous magnesium sulfate
6. customthe solvent was evaporated
7. dissolutionThe residue was dissolved in 25 ml of methylene chloride
8. addition5 ml of trifluoroacetic acid was added
9. stirringby stirring at room temperature for 1 hour
10. customAfter removing the solvent
11. distillationby distillation
12. additionthe residue was diluted with 40 ml of ethyl acetate
13. washThe mixture was sequentially washed with saturated aqueous sodium hydrogencarbonate solution and brine
14. dry with materialdried over anhydrous magnesium sulfate
15. customthe solvent was evaporated
16. customThe crude product was purified
17. customseparated by silica gel column chromatography (ethyl acetate:toluene=1:19 to 1:9)