Sulfuric Acid → 8-chloro-5-((E)-2-(5-(trifluoromethyl)pyridin-3-yl)vinyl)-2,3,4,5-tetrahydro-2-methyl-1H-pyrido[4,3-b]indole

HRID 1401452노트

반응식

HRID 1401452 반응식
[Cl:1][C:2]1[CH:10]=[CH:9][C:8]2[N:7]([CH2:11][CH:12]([C:14]3[CH:15]=[N:16][CH:17]=[C:18]([C:20]([F:23])([F:22])[F:21])[CH:19]=3)O)[C:6]3[CH2:24][CH2:25][N:26]([CH3:28])[CH2:27][C:5]=3[C:4]=2[CH:3]=1.S(=O)(=O)(O)O.[OH-].[K+]>>[Cl:1][C:2]1[CH:10]=[CH:9][C:8]2[N:7](/[CH:11]=[CH:12]/[C:14]3[CH:15]=[N:16][CH:17]=[C:18]([C:20]([F:21])([F:23])[F:22])[CH:19]=3)[C:6]3[CH2:24][CH2:25][N:26]([CH3:28])[CH2:27][C:5]=3[C:4]=2[CH:3]=1

참가 물질

4

반응물 3

HCID 1118Sulfuric AcidHCID 14797Potassium HydroxideHCID 578762152-(8-Chloro-1,2,3,4-tetrahydro-2-methylpyrido[4,3-b]indol-5-yl)-1-(5-(trifluoromethyl) pyridin-3-yl)ethanol

생성물 1

HCID 594549398-chloro-5-((E)-2-(5-(trifluoromethyl)pyridin-3-yl)vinyl)-2,3,4,5-tetrahydro-2-methyl-1H-pyrido[4,3-b]indole

반응 조건

온도
5 °C

실험 절차

2-(8-Chloro-1,2,3,4-tetrahydro-2-methylpyrido[4,3-b]indol-5-yl)-1-(5-(trifluoromethyl)pyridin-3-yl)ethanol (1 equiv.) is refluxed with 25% sulfuric acid for 2 h. The reaction mixture is cooled to 5° C. with an ice-water bath. KOH (15% aq. solution) is added dropwise to the reaction mixture until pH 9-10 is achieved. The reaction mixture is extracted with EtOAc. The combined organic layers are washed with water followed by brine, dried over sodium sulfate and evaporated under vacuum. The crude product is purified by column chromatography over silica gel (100-200 mesh) using a gradient of MeOH-EtOAc (0-10%).

후처리

  1. extractionThe reaction mixture is extracted with EtOAc
  2. washThe combined organic layers are washed with water
  3. dry with materialdried over sodium sulfate
  4. customevaporated under vacuum
  5. customThe crude product is purified by column chromatography over silica gel (100-200 mesh)

출처 및 근거

ORD 기록
ord-1ed0c0ba34a54b8fa2c78bb4ee24499b
출처 데이터셋
uspto-grants-2014_12
특허 번호
US08907097B2

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