반응 #313219

반응 방정식

HCl

1,5-dimethyl-1H-indole

n-Bu—Li

NaOH

B(OMe)3

→

title compound

수율 12.0%

1,5-Dimethyl-1H-indole-2-boronic Acid

수율 12.0%

용매

THF

반응 조건

후처리

1. 1
   온도The solution is cooled to 0° C.
2. 2
   온도The solution is warmed to ambient temperature
3. 3
   workup.STIRRINGstirred overnight
4. 4
   추출The aqueous phase is extracted with EtOAc (2×30 mL)
5. 5
   세척The combined organic layers are washed with brine
6. 6
   건조dried over MgSO4
7. 7
   여과filtered
8. 8
   농축concentrated
9. 9
   기타The solids are triturated with hexane
10. 10
    기타recrystallized from toluene/hexane

실험 절차

To a 0° C. solution of 1,5-dimethyl-1H-indole (1.10 g, 7.58 mmol) and THF (15 mL) is added 1.6M n-Bu—Li (5.7 mL, 9.09 mmol) the solution is warmed to ambient temperature and stirred for 1 h. The solution is cooled to 0° C. and B(OMe)3 (1.01 mL, 9.09 mmol) is added. The solution is warmed to ambient temperature and stirred overnight. 1M HCl (20 mL) is added and the pH adjusted to 7 with 1M NaOH. The aqueous phase is extracted with EtOAc (2×30 mL). The combined organic layers are washed with brine, dried over MgSO4, filtered and concentrated. The solids are triturated with hexane, and recrystallized from toluene/hexane to furnish the title compound (0.17 g, 0.90 mmol, 12%). 1H NMR (CDCl3), δ 2.38 (s, 3H), 4.08 (s, 3H), 6.91 (s, 1H), 6.99 (d, J=8.9 Hz, 1H), 7.29-7.38 (m, 2H) ppm. LC/MS (m/z): calcd. for C10H12BNO2 (M+H)+: 190.1. found: 146.1.

출처