反应详情

To a solution of 3,4-dichlorobenzyl alcohol (500 mg, 2.8 mmol) in THF (20 mL) was added sodium hydride (113 mg, 2.8 mmol, 60% dispersion in mineral oil) and stirred at room temperature for 2 hours and then at 50° C. for 30 minutes. Cooled to room temperature and the solvent removed in vacuo to afford an orange solid. This was dissolved in DMSO (5 mL) to which was added a solution of N-[(dimethylamino)sulfonyl]-4-fluorobenzamide (Preparation 11, 580 mg, 2.3 mmol) in DMSO (10 mL) slowly. The dark red solution was heated at 50° C. for 18 h then 120° C. for 2 hours. The mixture was cooled and poured onto water (50 mL) containing 2M HCl (30 mL) and extracted with EtOAc (2×30 mL), washed with 1M HCl (30 mL) and dried over MgSO4, filtered and solvent removed in vacuo to give 1.9 g of crude residue that was purified using reverse phase preparative HPLC to afford the title compound.

1. waitat 50° C. for 30 minutes
2. temperatureCooled to room temperature
3. customthe solvent removed in vacuo
4. customto afford an orange solid
5. temperatureThe dark red solution was heated at 50° C. for 18 h
6. wait120° C. for 2 hours
7. temperatureThe mixture was cooled
8. additionpoured onto water (50 mL)
9. extractionextracted with EtOAc (2×30 mL)
10. washwashed with 1M HCl (30 mL)
11. dry with materialdried over MgSO4
12. filtrationfiltered
13. customsolvent removed in vacuo
14. customto give 1.9 g of crude residue that
15. customwas purified