反应详情

温度

-78 °C

n-BuLi (0.58 mL, 0.93 mmol) was added dropwise to a solution of 1,3-difluorobenzene (0.102 mL, 0.1 mmol) in THF (5 mL) cooled to −78° C. and allowed to stir for 1 hour. tert-butyl 6-(3,5-dimethylisoxazol-4-yl)-2-ethoxy-4-formyl-1H-benzo[d]imidazole-1-carboxylate (200 mg, 0.52 mmol) in THF was added and the reaction was allowed to stir for 5 mins at −78° C., quenched with ammonium chloride, extracted with EtOAc and concentrated. The crude was then taken up in DCM (2 mL), Des-Martin periodinane (290 mg, 0.78 mmol) was added and the reaction was allowed to stir for 15 mins. The reaction was quenched with sat. Na2S2O3, extracted with EtOAc, concentrated and purified by silica gel chromatography to give tert-butyl 4-(2,6-difluorobenzoyl)-6-(3,5-dimethylisoxazol-4-yl)-2-ethoxy-1H-benzo[d]imidazole-1-carboxylate.

1. stirringto stir for 5 mins at −78° C.
2. customquenched with ammonium chloride
3. extractionextracted with EtOAc
4. concentrationconcentrated
5. additionDes-Martin periodinane (290 mg, 0.78 mmol) was added
6. stirringto stir for 15 mins
7. customThe reaction was quenched with sat. Na2S2O3
8. extractionextracted with EtOAc
9. concentrationconcentrated
10. custompurified by silica gel chromatography