Trimethylamine → N-(5-bromo-4-methylpyridin-2-yl)methanesulfonamide

HRID 1694761

Reaction equation

HRID 1694761 reaction equation
[Br:1][C:2]1[C:3]([CH3:9])=[CH:4][C:5]([NH2:8])=[N:6][CH:7]=1.CN(C)C.[CH3:14][S:15](Cl)(=[O:17])=[O:16]>C(Cl)Cl>[Br:1][C:2]1[C:3]([CH3:9])=[CH:4][C:5]([NH:8][S:15]([CH3:14])(=[O:17])=[O:16])=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 1146TrimethylamineHCID 31297Methanesulfonyl chlorideHCID 8176952-Amino-5-bromo-4-methylpyridine

Product 1

HCID 67280818N-(5-bromo-4-methylpyridin-2-yl)methanesulfonamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

5-Bromo-4-methylpyridin-2-amine (1.56 g) was dissolved in DCM (40 ml), trimethylamine (1.4 ml) added, followed by methanesulfonyl chloride (1.9 g) and the mixture stirred for 20 min. The solution was washed with water, dried (MgSO4) and evaporated. The residue was dissolved in THF, treated with TBAF, stirred for 16 h and evaporated. The residue was purified by chromatography on silica eluting with 27% EtOAc/isohexane. Yield 1.3 g. Carried forward to step (ii) without characterisation.

Workup

  1. washThe solution was washed with water
  2. dry with materialdried (MgSO4)
  3. customevaporated
  4. dissolutionThe residue was dissolved in THF
  5. additiontreated with TBAF
  6. stirringstirred for 16 h
  7. customevaporated
  8. customThe residue was purified by chromatography on silica eluting with 27% EtOAc/isohexane

Sources & evidence

ORD record
ord-e6ea66330efc4d8e98d63fafb5141d8a
Source dataset
uspto-grants-2012_04
Patent number
US08158820B2

Linked notes

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