Trimethylsilyl triflate → 3-(1H-pyrrol-2-ylmethylidene)-1H-indol-2-one

HRID 84787

반응식

HRID 84787 반응식
F[C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:11])[CH2:5]2.[Si](OS(C(F)(F)F)(=O)=O)(C)(C)C>C[Si](N[Si](C)(C)C)(C)C>[NH:7]1[CH:6]=[CH:5][CH:4]=[C:8]1[CH:9]=[C:5]1[C:4]2[C:8](=[CH:9][CH:10]=[CH:2][CH:3]=2)[NH:7][C:6]1=[O:11]

참가 물질

4

반응물 2

HCID 65367Trimethylsilyl triflateHCID 37310125-fluoro-1,3-dihydro-2H-indol-2-one

생성물 1

HCID 46253-(1H-pyrrol-2-ylmethylidene)-1H-indol-2-one수율 276.3%

시약·촉매·용매 1

HCID 13838Hexamethyldisilazane용매

실험 절차

(NH4)2SO4 (0.09 g, 0.67 mmol) was added into a stirred mixture of 8 (1.0 g, 6.61 mmol) in HMDS (20 mL, 20 P) at room temperature. The reaction mixture was then heated to reflux and maintained at that temperature for no less than 5 hours. Monitor the reaction by GC. After the reaction is completed, 14 (1.1 g, 3.77 mmol) and TMSOTf (0.29 g, 1.32 mmol) were added. Then the mixture was stirred, once the reaction was complete (as indicated by HPLC analysis) it was quenched with water (6 mL, 6 P.) and MeCN (30 mL). The mixture was filtrated and the filtrate cake was washed with MeCN (20 mL) and EtOH (5 mL), then it was dried under vacuum at 40° C. overnight to give the goal product 15 (1.92 g, 97% yield) as a yellow to brown powder with about 82.1% HPLC purity.

후처리

  1. temperatureThe reaction mixture was then heated
  2. temperatureto reflux
  3. temperaturemaintained at that temperature for no less than 5 hours
  4. customMonitor the reaction by GC
  5. customwas quenched with water (6 mL, 6 P.) and MeCN (30 mL)
  6. filtrationThe mixture was filtrated
  7. washthe filtrate cake was washed with MeCN (20 mL) and EtOH (5 mL)
  8. customit was dried under vacuum at 40° C. overnight

출처 및 근거

ORD 기록
ord-c7c44a9c0f534ed8b98c963570097c57
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08846953B2

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