反应详情

温度

23 °C

A solution of potassium tert-butoxide (1.84 g, 16.43 mmol) and 5-fluoro-2-methylindole (1.21 g, 8.09 mmol) in DMF (20 mL) is stirred under N2 at rt for 60 min. A solution of monochloroamine in ether (65 mL, 9.75 mmol) is added via an addition funnel over 10 min. The resulting mixture is stirred at 23° C. for 2 hours, and then concentrated in vacuo. The residue is partitioned between EtOAc and water. The organic phase is separated, washed with saturated aqueous NaHCO3, water and brine, dried (MgSO4), filtered and concentrated in vacuo. The residue is purified by silica gel chromatography eluting with 10% EtOAc in heptane to afford 5-fluoro-2-methyl-indol-1-ylamine (290 mg, 22%) as a solid. MS: 165 (M+H); 1H NMR (300 MHz, CDCl3): δ 7.24-7.19 (m, 1H), 7.12 (dd, 1H), 6.92 (dt, 1H), 6.12 (s, 1H), 4.23 (br s, 2 H), 2.39 (s, 3H).

1. concentrationconcentrated in vacuo
2. customThe residue is partitioned between EtOAc and water
3. customThe organic phase is separated
4. washwashed with saturated aqueous NaHCO3, water and brine
5. dry with materialdried (MgSO4)
6. filtrationfiltered
7. concentrationconcentrated in vacuo
8. customThe residue is purified by silica gel chromatography
9. washeluting with 10% EtOAc in heptane