2,6-Dibromopyridine → 2-Bromo-6-(methylthio)pyridine

HRID 2104997Notes

Reaction equation

HRID 2104997 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4](Br)[N:3]=1.[CH3:9][S-:10].[Na+]>CN(C=O)C.CCOC(C)=O>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([S:10][CH3:9])[N:3]=1

Participants

5

Reactant 2

HCID 122742,6-DibromopyridineHCID 4378561Sodium methanethiolate

Product 1

HCID 125608072-Bromo-6-(methylthio)pyridine

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2,6-dibromopyridine (200 mg, 0.844 mmol) in DMF (2 mL), was added sodium methanethiolate (65.1 mg, 0.929 mmol). The mixture was stirred at rt for 16 h, then was diluted with EtOAc. The organic phase was washed with water (2×) and brine, dried (Na2SO4) and concentrated. The crude residue was purified by flash chromatography (0 to 20% EtOAc/hexanes gradient) to afford Intermediate 165.1.

Workup

  1. washThe organic phase was washed with water (2×) and brine
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated
  4. customThe crude residue was purified by flash chromatography (0 to 20% EtOAc/hexanes gradient)

Sources & evidence

ORD record
ord-eef98b4b58174b958b0a4ff5fc94c5a7
Source dataset
uspto-grants-2009_08
Patent number
US07576098B2

Reaction notes

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