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Potassium Carbonate → 3-methoxycarbonyl-1-(6-(trifluoromethyl)quinol-4-yl)-1H-indole

HRID 1869158
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HRID 1869158 반응식
C(=O)([O-])[O-].[K+].[K+].Cl[C:8]1[C:17]2[C:12](=[CH:13][CH:14]=[C:15]([C:18]([F:21])([F:20])[F:19])[CH:16]=2)[N:11]=[CH:10][CH:9]=1.[CH3:22][O:23][C:24]([C:26]1[C:34]2[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=2)[NH:28][CH:27]=1)=[O:25]>CN(C)C=O.C(OCC)(=O)C.O>[CH3:22][O:23][C:24]([C:26]1[C:34]2[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=2)[N:28]([C:8]2[C:17]3[C:12](=[CH:13][CH:14]=[C:15]([C:18]([F:21])([F:20])[F:19])[CH:16]=3)[N:11]=[CH:10][CH:9]=2)[CH:27]=1)=[O:25]
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 3

HCID 11430Potassium CarbonateHCID 589098Methyl indole-3-carboxylateHCID 27367114-Chloro-6-(trifluoromethyl)quinoline

생성물 1

HCID 689686183-methoxycarbonyl-1-(6-(trifluoromethyl)quinol-4-yl)-1H-indole수율 84.6%

시약·촉매·용매 3

HCID 962Water용매
HCID 6228
Dimethylformamide
용매
HCID 8857Ethyl Acetate용매

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온도
100 °C

실험 절차

1.04 g (7.5 mmol) of potassium carbonate and 0.695 g (3 mmol) of 4-chloro-6-(trifluoromethyl)quinoline are added to 0.525 g (3 mmol) of 3-methoxycarbonyl-1H-indole in 10 cm3 of dimethylformamide under an argon atmosphere. After stirring at a temperature in the region of 100° C. for 20 hours, the reaction mixture is cooled and diluted with 100 cm3 of ethyl acetate and 100 cm3 of water. The organic phase is separated off by settling and washed with twice 100 cm3 of water and 100 cm3 of saturated aqueous sodium chloride solution and then it is dried over magnesium sulphate, filtered and concentrated to dryness under reduced pressure (2.7 kPa), resulting in an orange-coloured oil. This oil is triturated in 20 cm3 of isopropyl ether and the resulting precipitate is filtered off, giving 0.94 g of 3-methoxycarbonyl-1-(6-(trifluoromethyl)quinol-4-yl)-1H-indole in the form of a yellow powder. Mass spectrum (EI): m/e 370 (M+•), m/e 339.

후처리

  1. temperaturethe reaction mixture is cooled
  2. customThe organic phase is separated off by settling
  3. washwashed with twice 100 cm3 of water and 100 cm3 of saturated aqueous sodium chloride solution
  4. dry with materialit is dried over magnesium sulphate
  5. filtrationfiltered
  6. concentrationconcentrated to dryness under reduced pressure (2.7 kPa)
  7. customresulting in an orange-coloured oil
  8. customThis oil is triturated in 20 cm3 of isopropyl ether
  9. filtrationthe resulting precipitate is filtered off

출처 및 근거

ORD 기록
ord-1d8af05d6acb470bae4c56178f80013e
출처 데이터셋
uspto-grants-2009_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07638521B2

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