反应详情

A heavy-walled sealable 100 mL tube containing copper (I) iodide (0.088 g, 0.46 mmol), potassium carbonate (1.57 g, 11.4 mmol) and 6,7,9-trifluoro-1,5-dihydro-benzo[b]azepin-2-one (1.02 g, 4.74 mmol, prepared from commercially available 2-bromo-3,4,6-trifluoroaniline via application of Steps 1-3 of the procedure used for the synthesis of Examples 73 and 74) was fitted with a stirbar and septa and flushed with nitrogen. Toluene (5.0 mL), N,N′-dimethylethylene diamine (0.10 mL, 0.93 mmol) and vinyl bromide (10.0 mL, 1.0 M solution in tetrahydrofuran (THF), 10.0 mmol) were then added, in that order. The septa was removed, the reaction vessel was sealed tightly with a teflon screwcap and then placed in a pre-heated 110° C. oil bath. After 24 hours, the reaction was cooled to room temperature, poured into 1:1 H2O:saturated aqueous NaCl solution (50 mL) and extracted with methylene chloride (3×30 mL). The organic extracts were combined, dried over MgSO4, filtered and concentrated in vacuo to give an oil that was purified via flash chromatography on silica gel (0% to 30% ethyl acetate/hexanes linear gradient) to give the desired product.

1. customused for the synthesis of Examples 73 and 74)
2. customwas fitted with a stirbar and septa
3. customflushed with nitrogen
4. customThe septa was removed
5. customthe reaction vessel was sealed tightly with a teflon screwcap
6. customplaced in a pre-heated 110° C.
7. additionpoured into 1:1 H2O
8. extractionsaturated aqueous NaCl solution (50 mL) and extracted with methylene chloride (3×30 mL)
9. dry with materialdried over MgSO4
10. filtrationfiltered
11. concentrationconcentrated in vacuo
12. customto give an oil that
13. customwas purified via flash chromatography on silica gel (0% to 30% ethyl acetate/hexanes linear gradient)