反应详情

To 4-(1-(4-fluorophenyl)-1H-indazol-5-yl)tetrahydro-2H-pyran-4-ol (125 mg, 0.40 mmol) in 5 mL of DCE was added TiCl4 (0.44 mmol; 0.44 mL of 1 M solution in DCM). A precipitate immediately formed. The reaction was concentrated in vacuo to approx 1 mL volume and treated with 1-methoxy-2-methyl-1-(trimethylsiloxy)propene (0.23 mL, 1.2 mmol) and the reaction became homogeneous and was complete. The reaction was quenched with NaHCO3, extracted 4× EtOAc, and combined organic layers were dried over MgSO4, filtered, and concentrated. The residue was purified by SiO2 chromatography using 25% EtOAc in hexanes to give methyl 2-(4-(1-(4-fluorophenyl)-1H-indazol-5-yl)tetrahydro-2H-pyran-4-yl)-2-methylpropanoate (155 mg, 99%). MS found: (M+H)+=397.

1. customA precipitate immediately formed
2. concentrationThe reaction was concentrated in vacuo to approx 1 mL volume
3. customThe reaction was quenched with NaHCO3
4. extractionextracted 4× EtOAc
5. dry with materialwere dried over MgSO4
6. filtrationfiltered
7. concentrationconcentrated
8. customThe residue was purified by SiO2 chromatography