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

HRID 2091187ノート

反応式

HRID 2091187 の反応式
[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

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 67868Benzene, 1-iodo-3-(trifluoromethyl)-HCID 667772781-(5-chloro-1H-indol-2-yl)heptan-1-one

生成物 1

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

試薬・触媒・溶媒 2

HCID 24593copper(I) bromide触媒HCID 13387N-methyl-2-pyrrolidone溶媒

反応条件

温度
180 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-63b93bbe090d4ca5b63c8163f05c29a6
出典データセット
uspto-grants-2013_05
特許番号
US08436043B2

反応ノート

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