Toluene → 4-(3-cyclohexylmethyl-1H-indol-5-yloxy)-3,5-bis-trifluoromethyl-phenylacetonitrile

HRID 1007493Notes

Reaction equation

HRID 1007493 reaction equation
[CH:1]1([CH2:7][C:8]2[C:16]3[C:11](=[CH:12][CH:13]=[C:14]([O:17][C:18]4[C:25]([C:26]([F:29])([F:28])[F:27])=[CH:24][C:21]([CH2:22]Br)=[CH:20][C:19]=4[C:30]([F:33])([F:32])[F:31])[CH:15]=3)[NH:10][CH:9]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[C-:34]#[N:35].[Na+].C1(C)C=CC=CC=1>CN(C)C=O.O>[CH:1]1([CH2:7][C:8]2[C:16]3[C:11](=[CH:12][CH:13]=[C:14]([O:17][C:18]4[C:25]([C:26]([F:29])([F:28])[F:27])=[CH:24][C:21]([CH2:22][C:34]#[N:35])=[CH:20][C:19]=4[C:30]([F:33])([F:32])[F:31])[CH:15]=3)[NH:10][CH:9]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

6

Reactant 3

HCID 1140TolueneHCID 8929Sodium CyanideHCID 226698794-(3-Cyclohexylmethyl-1H-indol-5-yloxy)-3,5-bis-trifluoromethyl-benzyl bromide

Product 1

HCID 226696744-(3-cyclohexylmethyl-1H-indol-5-yloxy)-3,5-bis-trifluoromethyl-phenylacetonitrile

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Preparation is carried out in analogy to the procedure of Example VIII from 0.85 g (1.59 mmol) of benzyl bromide from Example XXII with 0.1 g (1.99 mmol) of sodium cyanide in 5 ml of dimethylformamide and 0.5 ml of water at 50° C. in 1.5 hours. The chromatography of the crude product is carried out on silica gel 60 by means of toluene.

Workup

  1. customPreparation

Sources & evidence

ORD record
ord-c27f8a1de1a14e6d853be4c646c12199
Source dataset
uspto-grants-2004_09
Patent number
US06794406B2

Reaction notes

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