Potassium Hydroxide → 8-ethyl-5-(2-(4-(trifluoromethyl)-6-methylpyridin-3-yl)ethyl)-2,3,4,5-tetrahydro-2-methyl-1H-pyrido[4,3-b]indole

HRID 509799Notes

Reaction equation

HRID 509799 reaction equation
[CH2:1]([C:3]1[CH:11]=[CH:10][C:9]2[NH:8][C:7]3[CH2:12][CH2:13][N:14]([CH3:16])[CH2:15][C:6]=3[C:5]=2[CH:4]=1)[CH3:2].[F:17][C:18]([F:29])([F:28])[C:19]1[C:24]([CH:25]=[CH2:26])=[CH:23][N:22]=[C:21]([CH3:27])[CH:20]=1.[OH-].[K+]>CN1C(=O)CCC1>[CH2:1]([C:3]1[CH:11]=[CH:10][C:9]2[N:8]([CH2:26][CH2:25][C:24]3[CH:23]=[N:22][C:21]([CH3:27])=[CH:20][C:19]=3[C:18]([F:29])([F:17])[F:28])[C:7]3[CH2:12][CH2:13][N:14]([CH3:16])[CH2:15][C:6]=3[C:5]=2[CH:4]=1)[CH3:2]

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 594550988-Ethyl-2-methyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indoleHCID 68734541Pyridine, 5-ethenyl-2-methyl-4-(trifluoromethyl)-

Product 1

HCID 578759038-ethyl-5-(2-(4-(trifluoromethyl)-6-methylpyridin-3-yl)ethyl)-2,3,4,5-tetrahydro-2-methyl-1H-pyrido[4,3-b]indole

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

The title compound is prepared from a mixture of 8-ethyl-2,3,4,5-tetrahydro-2-methyl-1H-pyrido[4,3-b]indole, 4-(trifluoromethyl)-2-methyl-5-vinylpyridine and KOH (5-7 equiv) in NMP at a temperature ranging between 25 deg C. to 100 deg C. The product obtained is isolated by preparative HPLC.

Workup

  1. customranging between 25 deg C
  2. customto 100 deg C
  3. customThe product obtained
  4. customis isolated by preparative HPLC

Sources & evidence

ORD record
ord-ce73eda196974c0b84fa850099c434d8
Source dataset
uspto-grants-2015_08
Patent number
US09096591B2

Reaction notes

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