Sodium methanesulfinate → 3-Bromo-2-chloro-5-((methylsulfonyl)methyl)pyridine

HRID 633593Notes

Reaction equation

HRID 633593 reaction equation
[CH3:1][S:2]([O-:4])=[O:3].[Na+].[Br:6][C:7]1[C:8]([Cl:15])=[N:9][CH:10]=[C:11]([CH2:13]Br)[CH:12]=1>CN(C)C=O.O>[Br:6][C:7]1[C:8]([Cl:15])=[N:9][CH:10]=[C:11]([CH2:13][S:2]([CH3:1])(=[O:4])=[O:3])[CH:12]=1

Participants

5

Reactant 2

HCID 2733271Sodium methanesulfinateHCID 848198723-Bromo-5-(bromomethyl)-2-chloropyridine

Product 1

HCID 904175713-Bromo-2-chloro-5-((methylsulfonyl)methyl)pyridineYield 84.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
65 °C

Procedure

Sodium methanesulfinate (0.748 g, 7.32 mmol) and the product from Example 143A (1.9 g, 6.66 mmol) were combined in N,N-dimethylformamide (4.44 mL) and heated at 65° C. for 1 hour. The reaction mixture was cooled and diluted with 200 mL of cold water producing a precipitate that was collected by filtration and dried to constant mass affording the title compound (1.6 g, 84%).

Workup

  1. temperatureThe reaction mixture was cooled
  2. filtrationwas collected by filtration
  3. customdried to constant mass

Sources & evidence

ORD record
ord-29d94dafc13c4b9a8f9e4c87248892b3
Source dataset
uspto-grants-2016_04
Patent number
US09321764B2

Reaction notes

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