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

HRID 509801Notes

Reaction equation

HRID 509801 reaction equation
[CH:1]([C:4]1[CH:12]=[CH:11][C:10]2[NH:9][C:8]3[CH2:13][CH2:14][N:15]([CH3:17])[CH2:16][C:7]=3[C:6]=2[CH:5]=1)([CH3:3])[CH3:2].[F:18][C:19]([F:30])([F:29])[C:20]1[C:25]([CH:26]=[CH2:27])=[CH:24][N:23]=[C:22]([CH3:28])[CH:21]=1.[OH-].[K+]>CN1C(=O)CCC1>[F:30][C:19]([F:18])([F:29])[C:20]1[CH:21]=[C:22]([CH3:28])[N:23]=[CH:24][C:25]=1[CH2:26][CH2:27][N:9]1[C:10]2[CH:11]=[CH:12][C:4]([CH:1]([CH3:3])[CH3:2])=[CH:5][C:6]=2[C:7]2[CH2:16][N:15]([CH3:17])[CH2:14][CH2:13][C:8]1=2

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 594552192,3,4,5-tetrahydro-8-isopropyl-2-methyl-1H-pyrido[4,3-b]indoleHCID 68734541Pyridine, 5-ethenyl-2-methyl-4-(trifluoromethyl)-

Product 1

HCID 578759915-(2-(4-(trifluoromethyl)-6-methylpyridin-3-yl)ethyl)-2,3,4,5-tetrahydro-8-isopropyl-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 2,3,4,5-tetrahydro-8-isopropyl-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-a76d836be90946b28e63df987ca237b2
Source dataset
uspto-grants-2015_08
Patent number
US09096591B2

Reaction notes

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