Potassium Carbonate → 3-methoxycarbonyl-1-(2-(trifluoromethyl)quinol-4-yl)-1H-indole

HRID 1869154

반응식

HRID 1869154 반응식
C(=O)([O-])[O-].[K+].[K+].Cl[C:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[N:11]=[C:10]([C:18]([F:21])([F:20])[F:19])[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]=[CH:15][CH:16]=3)[N:11]=[C:10]([C:18]([F:21])([F:20])[F:19])[CH:9]=2)[CH:27]=1)=[O:25]

참가 물질

7

반응물 3

HCID 11430Potassium CarbonateHCID 589098Methyl indole-3-carboxylateHCID 27367094-Chloro-2-(trifluoromethyl)quinoline

생성물 1

HCID 689705923-methoxycarbonyl-1-(2-(trifluoromethyl)quinol-4-yl)-1H-indole수율 54%

시약·촉매·용매 3

HCID 962Water용매HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

반응 조건

온도
100 °C

실험 절차

1.04 g (7.5 mmol) of potassium carbonate and 0.695 g (3 mmol) of 4-chloro-2-(trifluoromethyl)quinoline are added to 0.526 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 0.6 g of 3-methoxycarbonyl-1-(2-(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-69445a605d934814a3a5766549698cb2
출처 데이터셋
uspto-grants-2009_12
특허 번호
US07638521B2

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