Trifluoroacetic acid → 6-Chloro-2-methyl-1h-indole

HRID 505079노트

반응식

HRID 505079 반응식
[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[C:7]([CH2:11]O)[NH:8]2)=[CH:4][CH:3]=1.FC(F)(F)C(O)=O.C([SiH](CC)CC)C>ClCCCl>[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[C:7]([CH3:11])[NH:8]2)=[CH:4][CH:3]=1

참가 물질

5

반응물 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 16115151(6-Chloro-1H-indol-2-yl)methanol

생성물 1

HCID 2715536-Chloro-2-methyl-1h-indole수율 27%

시약·촉매·용매 1

HCID 111,2-Dichloroethane용매

실험 절차

A solution of 1.60 g (8.81 mmol) (6-chloro-1H-indol-2-yl)-methanol in 5 ml 1,2-dichloroethane was added to a mixture of 80.0 ml trifluoroacetic acid and 32.0 ml triethylsilane at 65° C. After 5 min, the reaction mixture was cooled to room temperature and quenched with water. The pH was adjusted to 14 by the addition of aqueous sodium hydroxide solution (32%). The aqueous layer was extracted with tert-butyl methyl ether (3×200 ml). The combined organic layers were dried over sodium sulfate and concentrated in vacuo. The residue was purified by flash-chromatography (aminopropyl-modified silica gel, n-heptane/ethyl acetate) to give the title compound (0.39 g; 27%) as a white solid.

후처리

  1. customquenched with water
  2. additionThe pH was adjusted to 14 by the addition of aqueous sodium hydroxide solution (32%)
  3. extractionThe aqueous layer was extracted with tert-butyl methyl ether (3×200 ml)
  4. dry with materialThe combined organic layers were dried over sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by flash-chromatography (aminopropyl-modified silica gel, n-heptane/ethyl acetate)

출처 및 근거

ORD 기록
ord-8e7f369070bc44b296c86536104f6ee6
출처 데이터셋
uspto-grants-2010_08
특허 번호
US07781436B2

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