反应详情

Dissolve 5-bromo-2-fluoro-phenylamine (1.40 g, 7.37 mmol), N,N-dimethylamino-4-pyridine (90 mg, 0.737 mmol), and methanesulfonyl chloride (1.69 g, 14.74 mmol) in CH2Cl2 (10 mL) and pyridine (10 mL). Stir under N2 for 4 h and concentrate in-vacuo. Dilute residue with 1.00N aqueous HCl (20 mL) and extract into ethyl acetate. Dry (MgSO4) and concentrate organics to a yellow solid. Dissolve in THF (20 mL) and add 1.0M tetrabutylammonium fluoride/THF (4.83 mL, 4.83 mmol). Heat to reflux for 3 h, then add H2O and brine. Extract into ethyl acetate, then dry (MgSO4) and concentrate organics to a white solid. Recrystallization from boiling toluene/hexanes affords 768 mg (39%) of the title compound as a white solid. MS (ES) 267 (M−H); HPLC shows 100% purity.

1. concentrationconcentrate in-vacuo
2. extractionDilute residue with 1.00N aqueous HCl (20 mL) and extract into ethyl acetate
3. dry with materialDry (MgSO4)
4. concentrationconcentrate organics to a yellow solid
5. dissolutionDissolve in THF (20 mL)
6. temperatureHeat
7. temperatureto reflux for 3 h
8. extractionExtract into ethyl acetate
9. dry with materialdry (MgSO4)
10. concentrationconcentrate organics to a white solid
11. customRecrystallization