Dimethyl Sulfoxide → 5-(3-Cyanopyridin-2-yloxy)-2-fluorobenzoic acid

HRID 883035Notes

Reaction equation

HRID 883035 reaction equation
Cl[C:2]1[N:9]=[CH:8][CH:7]=[CH:6][C:3]=1[C:4]#[N:5].[F:10][C:11]1[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][C:12]=1[C:13]([OH:15])=[O:14].C(=O)([O-])[O-].[Cs+].[Cs+].CS(C)=O>O>[C:4]([C:3]1[C:2]([O:20][C:17]2[CH:18]=[CH:19][C:11]([F:10])=[C:12]([CH:16]=2)[C:13]([OH:15])=[O:14])=[N:9][CH:8]=[CH:7][CH:6]=1)#[N:5]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 10796Cesium carbonateHCID 810792-ChloronicotinonitrileHCID 27744802-Fluoro-5-hydroxybenzoic acid

Product 1

HCID 691662995-(3-Cyanopyridin-2-yloxy)-2-fluorobenzoic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
95 °C

Procedure

To 2-chloronicotinonitrile (900 mg, 6.50 mmol), 2-fluoro-5-hydroxybenzoic acid (1.0 g, 6.4 mmol) and cesium carbonate (4.2 g, 13 mmol) was added DMSO (7 mL). The mixture was heated to 95° C. for 18 hours in a sealed tube. The mixture was diluted with water and extracted with EtOAc. The aqueous layer was acidified with 6 N HCl (pH˜2) and then extracted with EtOAc. The organic layer was dried over anhydrous sodium sulfate, filtered and concentrated to yield 5-(3-cyanopyridin-2-yloxy)-2-fluorobenzoic acid. MS m/z 257=[M+H]+. Calc'd for C13H7FN2O3: 258.21.

Workup

  1. extractionextracted with EtOAc
  2. extractionextracted with EtOAc
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-d7fc3e1313b047f0bf207d50f7dca26b
Source dataset
uspto-grants-2012_08
Patent number
US08236823B2

Reaction notes

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