反应详情

Zinc dust (200 mg, 3.08 mmol) is added to a flask and heated with a heat gun under high vacuum to remove moisture. DMF (1.0 mL, freshly distilled) is added under argon. 1,2-Dibromoethane (0.02 mL) is added and heated with heat gun until bubbling is observed. After it is cooled to RT, TMSCl (0.02 mL) is added and the mixture is stirred at RT for 20 min. Then a solution of methanesulfonic acid 2-iodomethyl-5-methylphenyl ester (224 mg, 0.688 mmol) in DMF (0.6 mL, freshly distilled) is added and the mixture is heated at 40° C. for 45 min. Then it is cooled to RT. Pd2(dba)3 (20 mg, 0.02 mmol), P(o-tolyl)3 (28.4 mg, 0.10 mmol) is added followed by a solution of 5-(2-benzyloxy-6-fluoro-4-iodophenyl)-2-benzyloxymethyl-1,1-dioxo-1,2,5-thiadiazolidin-3-one (200 mg, 0.344 mmol) in DMF (1.4 mL, freshly distilled). The mixture is stirred at RT for 2 h. ETOAc is added and it is filtered through Celite. The filtrate is then washed with 1N HCl solution, water and brine. It is then dried and concentrated. The residue is purified to give the title compound.

1. temperatureheated with a heat gun under high vacuum
2. customto remove moisture
3. distillationDMF (1.0 mL, freshly distilled)
4. additionis added under argon
5. addition1,2-Dibromoethane (0.02 mL) is added
6. temperatureheated
7. temperaturewith heat gun
8. customuntil bubbling
9. additionTMSCl (0.02 mL) is added
10. additionis added
11. temperaturethe mixture is heated at 40° C. for 45 min
12. temperatureThen it is cooled to RT
13. distillationfreshly distilled)
14. stirringThe mixture is stirred at RT for 2 h
15. additionETOAc is added
16. filtrationit is filtered through Celite
17. washThe filtrate is then washed with 1N HCl solution, water and brine
18. customIt is then dried
19. concentrationconcentrated
20. customThe residue is purified