反应详情

温度

100 °C

A solution of N-but-2-enyl-2,2,2-trifluoro-N-(2-iodo-4-trifluoromethyl-phenyl)-acetamide (12.7 g, 29 mmol) in DMF (60 mL) is treated with n-Bu4NCl (8.8 g, 32 mmol), Pd(OAc)2 (131 mg, 0.58 mmol), and stirred at 100° C. for 2 h. The mixture is cooled to rt, diluted with EtOAc (150 mL), filtered through a pad of silica gel, and washed with 1 M HCl (150 mL). The organic layer is separated, dried (Na2SO4), filtered and concentrated in vacuo. The residue is purified by silica gel chromatography eluting with 10%-30% EtOAc in heptane to afford 3-ethyl-5-trifluoromethyl-1H-indole (2.6 g, 42%). MS: 214 (M+H); 1H NMR (300 MHz, CDCl3): δ 8.08 (s, NH, 1H), 7.89 (s, 1H), 7.41 (m, 2H), 7.07 (m, 1H), 2.81 (q, 2H), 1.34 (t, 3H).

1. temperatureThe mixture is cooled to rt
2. filtrationfiltered through a pad of silica gel
3. washwashed with 1 M HCl (150 mL)
4. customThe organic layer is separated
5. dry with materialdried (Na2SO4)
6. filtrationfiltered
7. concentrationconcentrated in vacuo
8. customThe residue is purified by silica gel chromatography
9. washeluting with 10%-30% EtOAc in heptane