反应详情

4-[6-chloro-5-(trifluoromethyl)-1H-1,3-benzodiazol-2-yl]butan-1-ol (5.88 g, 20.09 mmol) was dissolved in DMF (50 ml) and anhydrous potassium carbonate (3.47 g, 25.11 mmol) was added at r.t. under N2 and the reaction stirred for 1 hr. SEM-Cl (3.92 ml, 22.10 mmol) was added and the reaction stirred for 3 hrs. The reaction mixture was concentrated in vacuo, EtOAc (150 ml) was added and the mixture was washed with 50% sat. brine solution (3×200 ml). The organic layer was dried over Na2SO4, filtered, and concentrated in vacuo to give the crude product. The product was purified by silica flash column chromatography eluting with MeOH:DCM (1:99-6:94) to give the product as a light orange oil (4.95 g, 58%): MS (ESI+) for C18H26ClF3N2O2Si m/z 424.40 [M+H]+; LC purity 81% (ret. time, 2.41 min); 1H NMR (500 MHz, CHLOROFORM-d) δ ppm −0.11-0.01 (9H, m), 0.66-1.12 (2H, m), 1.60-1.87 (2H, m), 2.07 (2H, td, J=7.33, 2.05 Hz), 2.91-3.21 (2H, m), 3.43-3.61 (2H, m), 3.70 (2H, d, J=4.10 Hz), 5.49 (2H, d, J=17.81 Hz), 7.45-8.15 (2H, m)

1. stirringthe reaction stirred for 3 hrs
2. concentrationThe reaction mixture was concentrated in vacuo, EtOAc (150 ml)
3. additionwas added
4. washthe mixture was washed with 50% sat. brine solution (3×200 ml)
5. dry with materialThe organic layer was dried over Na2SO4
6. filtrationfiltered
7. concentrationconcentrated in vacuo
8. customto give the crude product
9. customThe product was purified by silica flash column chromatography
10. washeluting with MeOH:DCM (1:99-6:94)