Hydrochloric Acid → 7-(Trifluoromethyl)-1H-indole

온도

-20 °C

To a stirred mixture of 7-trifluoromethyl-1H-indole-2,3-dione (116 mg) in THF (5.00 mL) was added boron trifluoride etherate (0.205 mL, 1.62 mmol) followed by sodium borohydride (71.4 mg, 1.88 mmol). The resulting mixture was stirred at −20° C. for 2 hrs, then water (1 mL) was added and the mixture was stirred at 0° C. for 10 min. The solution was acidified to pH=1 with 2N HCl, warmed to r.t. and stirred at r.t. for 20 min prior to extraction with EtOAc. The extracts were dried over magnesium sulphate, concentrated in vacuo and the residue purified by chromatography over silica gel eluting with hexane to give 7-trifluoromethyl-1H-indole. 1H NMR (400 MHz, CDCl3) δ ppm 6.63-6.68 (1 H, m), 7.20 (1 H, t, J=7.71 Hz), 7.30-7.35 (1 H, m), 7.47 (1 H, d, J=7.33 Hz), 7.83 (1 H, d, J=8.08 Hz), and 8.56 (1 H, br. s.).

1. stirringthe mixture was stirred at 0° C. for 10 min
2. temperaturewarmed to r.t.
3. stirringstirred at r.t. for 20 min
4. extractionto extraction with EtOAc
5. dry with materialThe extracts were dried over magnesium sulphate
6. concentrationconcentrated in vacuo
7. customthe residue purified by chromatography over silica gel eluting with hexane

ORD 기록

ord-f98f5bbd23374a47b90ad3d01b796d25

출처 데이터셋

uspto-grants-2012_11

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US08314111B2