1,2-Dimethoxyethane → 6-Methoxy-4-vinylquinoline-3-carbonitrile

HRID 638972Notes

Reaction equation

HRID 638972 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[CH:4][C:3]=1[C:14]#[N:15].C(=O)([O-])[O-].[K+].[K+].CO[CH2:24][CH2:25]OC>O>[CH:24]([C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[CH:4][C:3]=1[C:14]#[N:15])=[CH2:25]

Participants

5

Reactant 3

HCID 80711,2-DimethoxyethaneHCID 11430Potassium CarbonateHCID 224667634-Chloro-6-methoxy-quinoline-3-carbonitrile

Product 1

HCID 590262116-Methoxy-4-vinylquinoline-3-carbonitrileYield 86%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
85 °C

Procedure

To a solution of 4-chloro-6-(methyloxy)-3-quinolinecarbonitrile (1.1 g, 5.03 mmol), potassium carbonate (0.76 g, 5.53 mmol), tetrakis-triphenylphosphine (120 mg, 0.10 mmol) in DME (30 mL) and H2O (10 mL) was added 2,4,6-trivinylcycloborane-pyridine complex (1.33 g, 5.53 mmol). After stirring for 5 hours at 85° C. the reaction contents was concentrated and the product purified by chromatography on silica gel (hexanes/EtOAc, 4:1) to give a light brown solid (0.9 g, 86%): LC/MS (ES) m/e 211 (M+H)+.

Workup

  1. customthe reaction contents
  2. concentrationwas concentrated
  3. customthe product purified by chromatography on silica gel (hexanes/EtOAc, 4:1)

Sources & evidence

ORD record
ord-d7ec2237ba244b49a568b27b1285a653
Source dataset
uspto-grants-2010_04
Patent number
US07691850B2

Reaction notes

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