Cesium fluoride → 4-(4-Fluoro-6-methoxyquinolin-2-yl)benzonitrile

HRID 1472659Notes

Reaction equation

HRID 1472659 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]=[C:4]([C:14]2[CH:21]=[CH:20][C:17]([C:18]#[N:19])=[CH:16][CH:15]=2)[CH:3]=1.[F-:22].[Cs+]>[N+](CCCC)(CCCC)(CCCC)CCCC.[Br-].CS(C)=O>[F:22][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[C:4]([C:14]2[CH:21]=[CH:20][C:17]([C:18]#[N:19])=[CH:16][CH:15]=2)[CH:3]=1

Participants

5

Reactant 2

HCID 25953Cesium fluorideHCID 669800504-(4-Chloro-6-methoxyquinolin-2-yl)benzonitrile

Product 1

HCID 669800654-(4-Fluoro-6-methoxyquinolin-2-yl)benzonitrileYield 31.7%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of 4-(4-chloro-6-methoxyquinolin-2-yl)benzonitrile (See Example 11, step 1) (1 g, 3.4 mmol), CsF (5.2 g, 34 mmol), and n-Bu4NBr (109 mg, 0.34 mmol) in DMSO (10 mL) was heated to 150° C. for 2 h. An aqueous/EtOAC workup was followed by purification by column chromatography (PE/EA=10/1) to afford desired product (300 mg, 31.7%).

Workup

  1. customAn aqueous/EtOAC workup was followed by purification by column chromatography (PE/EA=10/1)

Sources & evidence

ORD record
ord-598c4aeabe62427cbf5c82ee70df24bb
Source dataset
uspto-grants-2015_04
Patent number
US09012646B2

Reaction notes

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