Tert-Butanesulfinamide → (+/-)-tert-Butyl 4-(1-((tert-butylsulfinyl)imino)-2,2,2-trifluoroethyl)-5-methoxy-7-methyl-1H-indole-1-carboxylate

온도

100 °C

To a solution of tert-butyl 5-methoxy-7-methyl-4-(2,2,2-trifluoroacetyl)-1H-indole-1-carboxylate (0.45 g, 1.26 mmol) and 2-methyl-2-propanesulfinamide (0.46 g, 3.78 mmol) in toluene (12.6 mL), Zr(O-t-Bu)4 (2.52 mL, 6.30 mmol) was added at room temperature, and the reaction was heated to 100° C. After 15 minutes the reaction mixture was cooled to room temperature and diluted with EtOAc and sat. aq. brine. The resulting mixture was filtered and the layers separated. The aqueous layer was extracted with EtOAc. The combined organic extracts were dried over MgSO4, filtered and concentrated. The resulting residue was purified by flash chromatography (0-50% EtOAc in heptanes) to provide the title compound. MS (ESI+) m/z 461.3 (M+H).

1. temperatureAfter 15 minutes the reaction mixture was cooled to room temperature
2. filtrationThe resulting mixture was filtered
3. customthe layers separated
4. extractionThe aqueous layer was extracted with EtOAc
5. dry with materialThe combined organic extracts were dried over MgSO4
6. filtrationfiltered
7. concentrationconcentrated
8. customThe resulting residue was purified by flash chromatography (0-50% EtOAc in heptanes)

ORD 기록

ord-ff8fdda6dc494e5cb2e5304e48998e3c

출처 데이터셋

uspto-grants-2015_06

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US09056874B2