Potassium Hydroxide → Ethyl 3-(6-(trifluoromethyl)pyridin-3-yl)-2-(1,2,3,4-tetrahydro-2,8-dimethylpyrido[4,3-b]indol-5-yl)propanoate

HRID 574517Notes

Reaction equation

HRID 574517 reaction equation
[CH3:1][N:2]1[CH2:15][CH2:14][C:5]2[NH:6][C:7]3[CH:8]=[CH:9][C:10]([CH3:13])=[CH:11][C:12]=3[C:4]=2[CH2:3]1.[F:16][C:17]([F:32])([F:31])[C:18]1[N:23]=[CH:22][C:21](/[CH:24]=[CH:25]\[C:26]([O:28][CH2:29][CH3:30])=[O:27])=[CH:20][CH:19]=1.[OH-].[K+]>CN1C(=O)CCC1>[F:31][C:17]([F:16])([F:32])[C:18]1[N:23]=[CH:22][C:21]([CH2:24][CH:25]([N:6]2[C:7]3[CH:8]=[CH:9][C:10]([CH3:13])=[CH:11][C:12]=3[C:4]3[CH2:3][N:2]([CH3:1])[CH2:15][CH2:14][C:5]2=3)[C:26]([O:28][CH2:29][CH3:30])=[O:27])=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 2092911H-Pyrido[4,3-b]indole, 2,3,4,5-tetrahydro-2,8-dimethyl-HCID 86634536(Z)-ethyl 3-(6-(trifluoromethyl)pyridin-3-yl)acrylate

Product 1

HCID 57876010Ethyl 3-(6-(trifluoromethyl)pyridin-3-yl)-2-(1,2,3,4-tetrahydro-2,8-dimethylpyrido[4,3-b]indol-5-yl)propanoate

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

The title compound is prepared from a mixture of 2,3,4,5-tetrahydro-2,8-dimethyl-1H-pyrido[4,3-b]indole, (Z)-ethyl 3-(6-(trifluoromethyl)pyridin-3-yl)acrylate 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-7fa7e0a0a2924fa79e71ca62a0e2557a
Source dataset
uspto-grants-2015_05
Patent number
US09034880B2

Reaction notes

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