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

HRID 335232

Reaction equation

HRID 335232 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-42fbcbf997444d6dadb900bddb096fd9
Source dataset
uspto-grants-2014_11
Patent number
US08883828B2

Linked notes

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