Sodium methanesulfinate → 8-Bromo-6-[(methanesulfonyl)methyl]quinoline

HRID 857273Notes

Reaction equation

HRID 857273 reaction equation
Br[CH2:2][C:3]1[CH:4]=[C:5]2[C:10](=[C:11]([Br:13])[CH:12]=1)[N:9]=[CH:8][CH:7]=[CH:6]2.[CH3:14][S:15]([O-:17])=[O:16].[Na+]>CN(C=O)C>[Br:13][C:11]1[CH:12]=[C:3]([CH2:2][S:15]([CH3:14])(=[O:17])=[O:16])[CH:4]=[C:5]2[C:10]=1[N:9]=[CH:8][CH:7]=[CH:6]2

Participants

4

Reactant 2

HCID 2733271Sodium methanesulfinateHCID 155413198-Bromo-6-(bromomethyl)quinoline

Product 1

HCID 98793738-Bromo-6-[(methanesulfonyl)methyl]quinoline

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 6-bromomethyl-8-bromoquinoline (1.0 eq) (described in International Patent Publication WO 94/22852) in of DMF (0.5M) was added sodium methanesulfinate (1.3 eq). After stirring overnight at room temperature, the resulting mixture was quenched with H2O (4× volume of DMF), stirred for one hour. The resulting precipitate was isolated by filtration and washed with Et2O to afford the 8-bromo-6-methanesulfonylmethyl-quinoline compound.

Workup

  1. customthe resulting mixture was quenched with H2O (4× volume of DMF)
  2. stirringstirred for one hour
  3. customThe resulting precipitate was isolated by filtration
  4. washwashed with Et2O

Sources & evidence

ORD record
ord-e63c257117aa48aea9afdf909c3d6837
Source dataset
uspto-grants-2006_12
Patent number
US07144896B2

Reaction notes

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