Hydrochloric Acid → 1-{5-chloro-1-[3-(trifluoromethyl)phenyl]-1H-indol-2-yl}heptan-1-one

HRID 2091187노트

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HRID 2091187 반응식
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([C:11](=[O:18])[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])=[CH:5]2.I[C:20]1[CH:21]=[C:22]([C:26]([F:29])([F:28])[F:27])[CH:23]=[CH:24][CH:25]=1.C(=O)([O-])[O-].[K+].[K+].Cl>[Cu]Br.CN1CCCC1=O>[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([C:20]1[CH:25]=[CH:24][CH:23]=[C:22]([C:26]([F:29])([F:28])[F:27])[CH:21]=1)[C:6]([C:11](=[O:18])[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])=[CH:5]2

참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 67868Benzene, 1-iodo-3-(trifluoromethyl)-HCID 66777278HCID 66777278, 화합물

생성물 1

HCID 667789981-{5-chloro-1-[3-(trifluoromethyl)phenyl]-1H-indol-2-yl}heptan-1-one수율 17%

시약·촉매·용매 2

HCID 24593copper(I) bromide촉매HCID 13387N-methyl-2-pyrrolidone용매

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온도
180 °C

실험 절차

A mixture of 1-(5-chloro-1H-indol-2-yl)heptan-1-one (9.14 g) synthesized above, 3-iodobenzotrifluoride (1.97 mL), copper (I) bromide (327 mg), potassium carbonate (2.36 g) and N-methyl-2-pyrrolidone (30 mL) was deaerated, and the mixture was stirred under argon atmosphere at 180° C. for 1 day. 1N Hydrochloric acid was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (10% ethyl acetate/hexane) to give the title object compound (0.78 g, 17%) as a brown oil.

후처리

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with saturated brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (10% ethyl acetate/hexane)

출처 및 근거

ORD 기록
ord-63b93bbe090d4ca5b63c8163f05c29a6
출처 데이터셋
uspto-grants-2013_05
특허 번호
US08436043B2

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