Pyridine → 5-bromo-4-chloro-2-fluoro-N-methyl-N-pyridin-2-yl-benzenesulfonamide

HRID 1891389Notes

Reaction equation

HRID 1891389 reaction equation
[Br:1][C:2]1[C:3]([Cl:13])=[CH:4][C:5]([F:12])=[C:6]([S:8](Cl)(=[O:10])=[O:9])[CH:7]=1.N1C=CC=CC=1.[CH3:20][NH:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][N:23]=1.[OH-].[Na+]>C(Cl)Cl>[Br:1][C:2]1[C:3]([Cl:13])=[CH:4][C:5]([F:12])=[C:6]([S:8]([N:21]([CH3:20])[C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][N:23]=2)(=[O:10])=[O:9])[CH:7]=1

Participants

6

Reactant 4

HCID 1049PyridineHCID 14798Sodium HydroxideHCID 207272-Pyridinamine, N-methyl-HCID 566047345-Bromo-4-chloro-2-fluoro-benzenesulfonyl chloride

Product 1

HCID 684721885-bromo-4-chloro-2-fluoro-N-methyl-N-pyridin-2-yl-benzenesulfonamideYield 31%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 5-bromo-4-chloro-2-fluorobenzenesulfonyl chloride (1.5 g, 4.89 mmol) in dry DCM (15 mL), at −20° C. was added pyridine (1.98 mL, 24.5 mmol) followed by methyl-pyridin-2-yl-amine (1.06 g, 9.78 mmol). The mixture was allowed to warm slowly to ambient temperature over 16 hrs. 1N NaOH solution (5 mL) was added and stirred for 15 mins. The mixture was extracted with DCM and the organics were washed with brine, dried over MgSO4 and the filtrate evaporated. The residue was purified by silica gel chromatography [eluent: 10% ethyl acetate in hexane] to give 5-bromo-4-chloro-2-fluoro-N-methyl-N-pyridin-2-yl-benzenesulfonamide as an oil (0.57 g, 31%). MS: 380.9 (M+H)+; tR=2.80 min (method 1).

Workup

  1. extractionThe mixture was extracted with DCM
  2. washthe organics were washed with brine
  3. dry with materialdried over MgSO4
  4. customthe filtrate evaporated
  5. customThe residue was purified by silica gel chromatography [eluent: 10% ethyl acetate in hexane]

Sources & evidence

ORD record
ord-af9b01acc8d444caab54d14b97c50a7b
Source dataset
uspto-grants-2013_08
Patent number
US08507536B2

Reaction notes

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