2-Chloro-4-fluorobenzene-1-sulfonyl chloride → N-(5-bromo-2-chloropyridin-3-yl)-2-chloro-4-fluorobenzenesulfonamide

HRID 1162480Notes

Reaction equation

HRID 1162480 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([NH2:9])[C:5]([Cl:8])=[N:6][CH:7]=1.C[Si]([N-][Si](C)(C)C)(C)C.[Na+].[Cl:20][C:21]1[CH:26]=[C:25]([F:27])[CH:24]=[CH:23][C:22]=1[S:28](Cl)(=[O:30])=[O:29]>C1COCC1.O>[Br:1][C:2]1[CH:3]=[C:4]([NH:9][S:28]([C:22]2[CH:23]=[CH:24][C:25]([F:27])=[CH:26][C:21]=2[Cl:20])(=[O:30])=[O:29])[C:5]([Cl:8])=[N:6][CH:7]=1

Participants

6

Reactant 3

HCID 5228462-Chloro-4-fluorobenzene-1-sulfonyl chlorideHCID 2724254Sodium bis(trimethylsilyl)amideHCID 218583543-Amino-5-bromo-2-chloropyridine

Product 1

HCID 57749435N-(5-bromo-2-chloropyridin-3-yl)-2-chloro-4-fluorobenzenesulfonamideYield 49%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a round-bottom flask, was added 5-bromo-2-chloropyridin-3-amine (0.2 g, 1.0 mmol, Asymchem Laboratories, Morrisville, N.C.) in THF (10 mL). To this solution, sodium bis(trimethylsilyl)amide (1M in THF, 3 mL, 3 mmol, Aldrich, St. Louis, Mo.) was added and the mixture was stirred for 5 minutes. Then 2-chloro-4-fluorobenzene-1-sulfonyl chloride (0.7 g, 3 mmol, Aldrich, St. Louis, Mo.) was added to the mixture and the suspension was stirred at 25° C. for 15 h. The mixture was diluted with H2O. The organic layer was collected by extracting the water with DCM (3×). The combined organic was dried over sodium sulfate and concentrated in vacuo. Purification by silica gel chromatography (1 to 30% EtOAc/CH2Cl2) gave N-(5-bromo-2-chloropyridin-3-yl)-2-chloro-4-fluorobenzenesulfonamide (0.190 g, 49% yield) as a tan oil. MS (ESI positive ion) m/z: 401 (M+1).

Workup

  1. stirringthe suspension was stirred at 25° C. for 15 h
  2. customThe organic layer was collected
  3. extractionby extracting the water with DCM (3×)
  4. dry with materialThe combined organic was dried over sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customPurification by silica gel chromatography (1 to 30% EtOAc/CH2Cl2)

Sources & evidence

ORD record
ord-8ec69da511b0497fa2ef6a819743ed8b
Source dataset
uspto-grants-2010_10
Patent number
US07820665B2

Reaction notes

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