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

HRID 1400375
Notes
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Reaction equation

HRID 1400375 reaction equation
[F:1][C:2]([F:28])([F:27])[C:3]1[CH:4]=[C:5]([CH:9](O)[CH2:10][N:11]2[C:19]3[CH:18]=[CH:17][C:16]([CH3:20])=[CH:15][C:14]=3[C:13]3[CH2:21][N:22]([CH3:25])[CH2:23][CH2:24][C:12]2=3)[CH:6]=[N:7][CH:8]=1.S(=O)(=O)(O)O.[OH-].[K+]>>[F:27][C:2]([F:1])([F:28])[C:3]1[CH:4]=[C:5](/[CH:9]=[CH:10]/[N:11]2[C:19]3[CH:18]=[CH:17][C:16]([CH3:20])=[CH:15][C:14]=3[C:13]3[CH2:21][N:22]([CH3:25])[CH2:23][CH2:24][C:12]2=3)[CH:6]=[N:7][CH:8]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 3

HCID 1118Sulfuric AcidHCID 14797Potassium HydroxideHCID 578760561-(5-(Trifluoromethyl)pyridin-3-yl)-2-(1,2,3,4-tetrahydro-2,8-dimethylpyrido[4,3-b]indol-5-yl)ethanol

Product 1

HCID 594550235-((E)-2-(5-(trifluoromethyl)pyridin-3-yl)vinyl)-2,3,4,5-tetrahydro-2,8-dimethyl-1H-pyrido[4,3-b]indole

Conditions

Temperature
5 °C

Procedure

1-(5-(Trifluoromethyl)pyridin-3-yl)-2-(1,2,3,4-tetrahydro-2,8-dimethylpyrido[4,3-b]indol-5-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%).

Workup

  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)

Sources & evidence

ORD record
ord-c14050ee446944a38d5a1ca28948dc94
Source dataset
uspto-grants-2014_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08906925B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes