反应详情

To a solution of 5,7-dimethyl-1-tosyl-1H-indole-4-carbaldehyde (Example 46-D) (500 mg, 1.53 mmol) in THF (15 mL) at −78° C., vinylmagnesium bromide (2.29 mL, 2.29 mmol) was added and the reaction was stirred for 15 minutes. At this point a saturated water solution of NH4Cl was added. The layers were separated and the aqueous layer was extracted with ethyl acetate. The combined organics were dried over MgSO4 and evaporated. The resulting residue was dissolved in DCM (4 mL), and Dess-Martin Periodinane (1.19 g, 2.81 mmol) was added. After 15 minutes the reaction was complete. The reaction was quenched with a sat. aq. solution of NaHCO3 and sodium thiosulfate. The layers were separated and the aqueous layer was extracted with DCM. It was purified using FCC eluting with heptane/EtOAc 1:1 to give the title compound. 1H NMR (400 MHz, DMSO-d6) δ 7.85 (d, J=3.79 Hz, 1H), 7.50-7.66 (m, J=8.34 Hz, 2H), 7.30-7.45 (m, J=8.34 Hz, 2H), 7.01 (s, 1H), 6.71 (dd, J=10.48, 17.56 Hz, 1H), 6.59 (d, J=4.04 Hz, 1H), 6.14 (d, J=10.86 Hz, 1H), 5.88 (d, J=17.43 Hz, 1H), 2.35 (s, 3H), 2.21 (s, 3H).

1. customThe layers were separated
2. extractionthe aqueous layer was extracted with ethyl acetate
3. dry with materialThe combined organics were dried over MgSO4
4. customevaporated
5. dissolutionThe resulting residue was dissolved in DCM (4 mL)
6. waitAfter 15 minutes the reaction was complete
7. customThe reaction was quenched with a sat. aq. solution of NaHCO3 and sodium thiosulfate
8. customThe layers were separated
9. extractionthe aqueous layer was extracted with DCM
10. customIt was purified
11. washeluting with heptane/EtOAc 1:1