Water → 3-(4-Fluorophenoxy)-5-(pyridin-2-ylthio)picolinonitrile

HRID 1511012Notes

Reaction equation

HRID 1511012 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[SH:7].[H-].[Na+].Br[C:11]1[CH:12]=[C:13]([O:19][C:20]2[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=2)[C:14]([C:17]#[N:18])=[N:15][CH:16]=1.O>CC(N(C)C)=O>[F:26][C:23]1[CH:22]=[CH:21][C:20]([O:19][C:13]2[C:14]([C:17]#[N:18])=[N:15][CH:16]=[C:11]([S:7][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=3)[CH:12]=2)=[CH:25][CH:24]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 669950285-Bromo-3-(4-fluorophenoxy)picolinonitrileHCID 178418616HCID 178418616, compound

Product 1

HCID 679944723-(4-Fluorophenoxy)-5-(pyridin-2-ylthio)picolinonitrileYield 70%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

To a solution of pyridine-2-thiol (2.5 g, 23 mmol) in DMA (25 mL) cooled to 0° C. was added NaH (0.90 g, 23 mmol) and the reaction stirred at ambient temperature for 20 min, followed by addition of the 5-bromo-3-(4-fluorophenoxy)picolinonitrile (6.6 g, 23 mmol) and stirring over night at ambient temperature. The reaction was poured into water (250 mL) and a solid formed. The solid was collected, washed with water, and dried in vacuo to yield 3-(4-fluorophenoxy)-5-(pyridin-2-ylthio)picolinonitrile (5 g, 16 mmol, 70%).

Workup

  1. stirringstirring over night at ambient temperature
  2. customa solid formed
  3. customThe solid was collected
  4. washwashed with water
  5. customdried in vacuo

Sources & evidence

ORD record
ord-9c2b719675664004aacc2521a5012e1f
Source dataset
uspto-grants-2012_07
Patent number
US08212045B2

Reaction notes

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