2-Methyl-5-vinylpyridine → 1H-Pyrido(4,3-b)indole, 2,3,4,5-tetrahydro-2-butyl-8-methyl-5-(2-(6-methyl-3-pyridyl)ethyl)-

HRID 1465412Notes

Reaction equation

HRID 1465412 reaction equation
[CH2:1]([N:5]1[CH2:18][CH2:17][C:8]2[NH:9][C:10]3[CH:11]=[CH:12][C:13]([CH3:16])=[CH:14][C:15]=3[C:7]=2[CH2:6]1)[CH2:2][CH2:3][CH3:4].[CH3:19][C:20]1[CH:25]=[CH:24][C:23]([CH:26]=[CH2:27])=[CH:22][N:21]=1.[OH-].[K+]>CN1C(=O)CCC1>[CH2:1]([N:5]1[CH2:18][CH2:17][C:8]2[N:9]([CH2:27][CH2:26][C:23]3[CH:22]=[N:21][C:20]([CH3:19])=[CH:25][CH:24]=3)[C:10]3[CH:11]=[CH:12][C:13]([CH3:16])=[CH:14][C:15]=3[C:7]=2[CH2:6]1)[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 88172-Methyl-5-vinylpyridineHCID 14797Potassium HydroxideHCID 593911HCID 593911, compound

Product 1

HCID 2098691H-Pyrido(4,3-b)indole, 2,3,4,5-tetrahydro-2-butyl-8-methyl-5-(2-(6-methyl-3-pyridyl)ethyl)-

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

The title compound is prepared from a mixture of 2-butyl-2,3,4,5-tetrahydro-8-methyl-1H-pyrido[4,3-b]indole, 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-d0455dbe1c5a478ea77586f89f3d31ce
Source dataset
uspto-grants-2015_04
Patent number
US08999978B2

Reaction notes

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