反应详情

A mixture of 2-methyl-1-(phenylsulfonyl)-4-(trifluoromethyl)-1H-indole (13.5 g, 39.82 mmol; step C above) and K2CO3 (27.5 g) in MeOH/H2O (2:1, 300 mL) was heated at reflux temperature. After 14 h the mixture was cooled and concentrated in vacuo. The residue was partitioned between Et2O/H2O, the layers were separated and the aqueous layer was extracted with Et2O (×2). Combined organics were washed (H2O, brine), dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified via column chromatography (SiO2, 1:1 EtOAc/hexanes eluent), affording 11.0 g of the deprotected indole as a yellow oil: 1H NMR (400 MHz, CDCl3) δ 7.43 (d, J=8.0 Hz, 1H), 7.35 (d, J=8.0 Hz, 1H), 7.15 (t, J=8.0 Hz, 1H), 6.46 (s, 1H), 2.48 (s, 3H); MS (ES) m/z 200 (M+1).

1. temperaturewas heated
2. temperatureat reflux temperature
3. temperatureAfter 14 h the mixture was cooled
4. concentrationconcentrated in vacuo
5. customThe residue was partitioned between Et2O/H2O
6. customthe layers were separated
7. extractionthe aqueous layer was extracted with Et2O (×2)
8. washCombined organics were washed (H2O, brine)
9. dry with materialdried over Na2SO4
10. filtrationfiltered
11. concentrationconcentrated in vacuo
12. customThe residue was purified via column chromatography (SiO2, 1:1 EtOAc/hexanes eluent)