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

HRID 509881Notes

Reaction equation

HRID 509881 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:28])([F:27])[C:19]1[CH:24]=[CH:23][N:22]=[CH:21][C:20]=1[CH:25]=[CH2:26].[OH-].[K+]>CN1C(=O)CCC1>[CH2:1]([C:3]1[CH:11]=[CH:10][C:9]2[N:8]([CH2:26][CH2:25][C:20]3[CH:21]=[N:22][CH:23]=[CH:24][C:19]=3[C:18]([F:28])([F:17])[F:27])[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 68735093Pyridine, 3-ethenyl-4-(trifluoromethyl)-

Product 1

HCID 578758778-ethyl-5-(2-(4-(trifluoromethyl)pyridin-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)-3-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-d527dfbc13b34fd09a4440036dae9c14
Source dataset
uspto-grants-2015_08
Patent number
US09096591B2

Reaction notes

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