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

HRID 1695715Notes

Reaction equation

HRID 1695715 reaction equation
[C:1]1([S:7](Cl)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Br:11][C:12]1[CH:13]=[C:14]([NH2:19])[C:15]([Cl:18])=[N:16][CH:17]=1.N1C=CC=CC=1>C(Cl)Cl>[Br:11][C:12]1[CH:13]=[C:14]([NH:19][S:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)(=[O:9])=[O:8])[C:15]([Cl:18])=[N:16][CH:17]=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 6344DichloromethaneSolvent

Procedure

Benzenesulfonyl chloride (2.24 ml, 17.5 mmol) was added dropwise over 5-10 mins to a solution of 5-bromo-2-chloro-3-pyridinamine (2.5 g, 12.1 mmol) and pyridine (1.5 ml, 18.56 mmol) in DCM (25 ml). The reaction was stirred for 18 h at RT before evaporation to dryness in vacuo. The residue was split in two and purified by silica gel chromatography, eluting with 0-100% DCM in cyclohexane. Appropriate fractions were combined and evaporated to give title compound, 1.81 g.

Workup

  1. customThe residue was split in two
  2. custompurified by silica gel chromatography
  3. washeluting with 0-100% DCM in cyclohexane
  4. customevaporated

Sources & evidence

ORD record
ord-e8842bfc8421442392d6bb583758f8ed
Source dataset
uspto-grants-2012_04
Patent number
US08163743B2

Reaction notes

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