Pyridine → 2-amino-5-bromo-N,N-dimethylpyridine-3-sulfonamide

HRID 734982

Reaction equation

HRID 734982 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[NH2:7].NC1C(Cl)=NC=C([Br:15])C=1.[N:17]1[CH:22]=CC=C[CH:18]=1.C1([S:29](Cl)(=[O:31])=[O:30])C=CC=CC=1>ClCCl>[NH2:7][C:2]1[C:3]([S:29]([N:17]([CH3:22])[CH3:18])(=[O:31])=[O:30])=[CH:4][C:5]([Br:15])=[CH:6][N:1]=1

Participants

6

Reactant 4

HCID 1049PyridineHCID 7369Benzenesulfonyl chlorideHCID 104392-AminopyridineHCID 218583543-Amino-5-bromo-2-chloropyridine

Product 1

HCID 523351532-amino-5-bromo-N,N-dimethylpyridine-3-sulfonamideYield 34%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of a pyridineamine such as 3-amino-5-bromo-2-chloropyridine (24 mmol) in dichloromethane (50 mL) was added pyridine (37 mmol) followed by benzenesulfonyl chloride (35 mmol) dropwise over 5 minutes. The reaction mixture was stirred at RT for 18 h and evaporated to dryness in vacuo. The residue was purified by flash chromatography on silica gel (15% hexanes in CH2Cl2 then 0 to 5% EtOAc in 15% hexanes in CH2Cl2). During evaporation of the solvents the product crashed out. The resultant slurry was diluted with hexanes, filtered and dried under vacuum to give the title compound (2.89 g, 34%) as a white solid. MS (ES) m/e 346.7 (M+H)+.

Workup

  1. customevaporated to dryness in vacuo
  2. customThe residue was purified by flash chromatography on silica gel (15% hexanes in CH2Cl2
  3. customDuring evaporation of the solvents the product
  4. additionThe resultant slurry was diluted with hexanes
  5. filtrationfiltered
  6. customdried under vacuum

Sources & evidence

ORD record
ord-3afc9affb6774934b835188b36274753
Source dataset
uspto-grants-2009_09
Patent number
US07592342B2

Linked notes

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