Potassium Cyanide → [6-[2-(3-Methoxypropyl)phenyl]-4-(trifluoromethyl)pyridin-3-yl]acetonitrile

HRID 2194899Notes

Reaction equation

HRID 2194899 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[C:12]1[CH:21]=[C:20]([C:22]([F:25])([F:24])[F:23])[C:15]([C:16](OC)=O)=[CH:14][N:13]=1.[C-:26]#[N:27].[K+]>CO>[CH3:1][O:2][CH2:3][CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[C:12]1[N:13]=[CH:14][C:15]([CH2:16][C:26]#[N:27])=[C:20]([C:22]([F:25])([F:23])[F:24])[CH:21]=1

Participants

4

Reactant 2

HCID 9032Potassium CyanideHCID 67447798Methyl 6-[2-(3-methoxypropyl)phenyl]-4-(trifluoromethyl)nicotinate

Product 1

HCID 67446419[6-[2-(3-Methoxypropyl)phenyl]-4-(trifluoromethyl)pyridin-3-yl]acetonitrile

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 5-(bromomethyl)-2-[2-(3-methoxypropyl)phenyl]-4-(trifluoromethyl)pyridine (1 eq.) from step 1 and KCN (5 eq.) in MeOH (0.08M) was stirred for 48 h at room temperature. The mixture was concentrated and purification by column chromatography on silica gel, eluting with Hex/EtOAc 30%, afforded the title desired material as an off-white solid.

Workup

  1. concentrationThe mixture was concentrated
  2. custompurification by column chromatography on silica gel
  3. washeluting with Hex/EtOAc 30%

Sources & evidence

ORD record
ord-87896958987448449dcdd864a49dd2b8
Source dataset
uspto-grants-2012_12
Patent number
US08334308B2

Reaction notes

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