Pyridine → N-(5-Bromo-2-chloropyridin-3-yl)benzenesulfonamide

HRID 81485Notes

Reaction equation

HRID 81485 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([NH2:9])[C:5]([Cl:8])=[N:6][CH:7]=1.[C:10]1([S:16](Cl)(=[O:18])=[O:17])[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.N1C=CC=CC=1>CN(C1C=CN=CC=1)C>[Br:1][C:2]1[CH:3]=[C:4]([NH:9][S:16]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)(=[O:18])=[O:17])[C:5]([Cl:8])=[N:6][CH:7]=1

Participants

5

Reactant 3

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

Product 1

HCID 57843322N-(5-Bromo-2-chloropyridin-3-yl)benzenesulfonamide

Reagents, catalysts & solvents 1

HCID 142844-(Dimethylamino)pyridineCatalyst

Procedure

A solution of DMAP (0.012 g, 0.096 mmol), 5-bromo-2-chloropyridin-3-amine (0.2 g, 0.96 mmol) and benzene sulfonyl chloride (0.61 ml, 4.8 mmol) in pyridine (0.16 ml, 1.92 mmol) is heated at 50° C. overnight. The reaction is cooled to room temperature and absorbed onto silica. Purification by flash chromatography (SiO2, 10-20% EtOAc in iso-hexane) yields N-(5-Bromo-2-chloro-pyridin-3-yl)-benzenesulfonamide as a white solid. [M+H]+ 347.

Workup

  1. customabsorbed onto silica
  2. customPurification by flash chromatography (SiO2, 10-20% EtOAc in iso-hexane)

Sources & evidence

ORD record
ord-c8a2526c15424bdd9b490199d166abad
Source dataset
uspto-grants-2014_09
Patent number
US08846687B2

Reaction notes

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