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 1465338Notes

Reaction equation

HRID 1465338 reaction equation
[F:1][C:2]([F:13])([F:12])[C:3]1[C:8]([CH:9]=[CH2:10])=[CH:7][N:6]=[C:5]([CH3:11])[CH:4]=1.[CH2:14]([C:16]1[CH:24]=[CH:23][C:22]2[NH:21][C:20]3[CH2:25][CH2:26][N:27]([CH3:29])[CH2:28][C:19]=3[C:18]=2[CH:17]=1)[CH3:15].[OH-].[K+]>CN1C(=O)CCC1>[CH2:14]([C:16]1[CH:24]=[CH:23][C:22]2[N:21]([CH2:10][CH2:9][C:8]3[CH:7]=[N:6][C:5]([CH3:11])=[CH:4][C:3]=3[C:2]([F:1])([F:12])[F:13])[C:20]3[CH2:25][CH2:26][N:27]([CH3:29])[CH2:28][C:19]=3[C:18]=2[CH:17]=1)[CH3:15]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 866915168-ethyl-2,3,4,5-tetrahydro-2-methyl-1H-pyrido[4,3-b]indole 4-(trifluoromethyl)-2-methyl-5-vinylpyridine

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-e7c638c0b76247cf8f18e5223f206e1a
Source dataset
uspto-grants-2015_04
Patent number
US08999978B2

Reaction notes

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