Dimethylformamide → 5-(3-Bromophenoxy)-3-(3-methoxyphenylthio)picolinonitrile

HRID 911911Notes

Reaction equation

HRID 911911 reaction equation
Br[C:2]1[CH:3]=[C:4]([S:10][C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([O:17][CH3:18])[CH:12]=2)[C:5]([C:8]#[N:9])=[N:6][CH:7]=1.[Br:19][C:20]1[CH:21]=[C:22]([OH:26])[CH:23]=[CH:24][CH:25]=1.CN(C=O)C.[H-].[Na+]>O>[Br:19][C:20]1[CH:21]=[C:22]([CH:23]=[CH:24][CH:25]=1)[O:26][C:2]1[CH:3]=[C:4]([S:10][C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([O:17][CH3:18])[CH:12]=2)[C:5]([C:8]#[N:9])=[N:6][CH:7]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 115633-BromophenolHCID 24758Sodium hydrideHCID 669947555-Bromo-3-(3-methoxyphenylthio)picolinonitrile

Product 1

HCID 669955395-(3-Bromophenoxy)-3-(3-methoxyphenylthio)picolinonitrileYield 81.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A 10 mL round-bottomed flask was charged with 5-bromo-3-(3-methoxyphenylthio)picolinonitrile (214 mg, 0.666 mmol), 3-bromophenol (138 mg, 0.800 mmol), and DMF (6 mL). NaH (24.0 mg, 0.999 mmol) was added and reaction stirred at room temperature for 24 hours. The reaction was poured into water and extracted with EtOAc. The organic layer was dried over sodium sulfate, filtered and concentrated. The resulting residue was purified on silica gel (10% EtOAc in Hexanes) to afford the title compound (225 mg, 81.7% yield).

Workup

  1. customreaction
  2. extractionextracted with EtOAc
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe resulting residue was purified on silica gel (10% EtOAc in Hexanes)

Sources & evidence

ORD record
ord-8ecb0a9c74b34b89b5c8af60c6b364e9
Source dataset
uspto-grants-2011_09
Patent number
US08022223B2

Reaction notes

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