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

HRID 2370387Notes

Reaction equation

HRID 2370387 reaction equation
[C:1]1([S:7](Cl)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH2:11][C:12]1[C:13]([Cl:19])=[N:14][CH:15]=[C:16]([Br:18])[CH:17]=1.N1C=CC=CC=1>C(Cl)Cl>[Br:18][C:16]1[CH:17]=[C:12]([NH:11][S:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)(=[O:9])=[O:8])[C:13]([Cl:19])=[N:14][CH:15]=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)benzenesulfonamideYield 9.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of benzenesulfonyl chloride (1.23 mL, 9.62 mmol, 2 eq) in DCM (50 mL) is added dropwise over 15 min to a solution of 3-amino-5-bromo-2-chloropyridine [Jouve, K.; Bergman, J., Journal of Heterocyclic Chemistry, (2003), 40(2), 261-268] (1 g, 4.81 mmol) and pyridine (1.94 ml, 24 mmol, 5 eq) in DCM (20 mL), under an argon atmosphere. The resulting mixture is stirred for 20 h at rt, concentrated, diluted with H2O and extracted with DCM. The organic phase is washed with brine, dried (Na2SO4), filtered and concentrated. The residue is purified by silica gel column chromatography (DCM) to afford 163 mg of the title compound as a white solid: ESI-MS: 346.9 [M−H]−; tR=4.33 min (System 1); TLC: Rf=0.23 (DCM).

Workup

  1. concentrationconcentrated
  2. additiondiluted with H2O
  3. extractionextracted with DCM
  4. washThe organic phase is washed with brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue is purified by silica gel column chromatography (DCM)

Sources & evidence

ORD record
ord-638cda6400c849008bfebecf68c17799
Source dataset
uspto-grants-2014_04
Patent number
US08710085B2

Reaction notes

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