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

HRID 1806158Notes

Reaction equation

HRID 1806158 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([N+]([O-])=O)[C:5]([C:8]#[N:9])=[N:6][CH:7]=1.[CH3:13][O:14][C:15]1[CH:16]=[C:17]([SH:21])[CH:18]=[CH:19][CH:20]=1.CN(C=O)C.[H-].[Na+]>O>[Br:1][C:2]1[CH:3]=[C:4]([S:21][C:17]2[CH:18]=[CH:19][CH:20]=[C:15]([O:14][CH3:13])[CH:16]=2)[C:5]([C:8]#[N:9])=[N:6][CH:7]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 849893-MethoxybenzenethiolHCID 27696985-Bromo-3-nitropyridine-2-carbonitrile

Product 1

HCID 669947555-Bromo-3-(3-methoxyphenylthio)picolinonitrileYield 82%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A 10 mL round-bottomed flask was charged with 5-bromo-3-nitropicolinonitrile (300 mg, 1.31 mmol), 3-methoxybenzenethiol (0.150 mL, 1.31 mmol), and DMF (12 mL). NaH (37.8 mg, 1.58 mmol) was added and reaction stirred at room temperature for 10 minutes. 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 (345 mg, 81%).

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-45f4e0e9f05e44ca8d549f807c95e249
Source dataset
uspto-grants-2013_01
Patent number
US08354540B2

Reaction notes

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