Pyridine → 4-Bromo-2-fluoro-N-thiazol-2-yl-benzenesulfonamide

HRID 1644625Notes

Reaction equation

HRID 1644625 reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[CH:5][N:6]=1.N1C=CC=CC=1.C(Cl)Cl.[Br:16][C:17]1[CH:22]=[CH:21][C:20]([S:23](Cl)(=[O:25])=[O:24])=[C:19]([F:27])[CH:18]=1>>[Br:16][C:17]1[CH:22]=[CH:21][C:20]([S:23]([NH:1][C:2]2[S:3][CH:4]=[CH:5][N:6]=2)(=[O:24])=[O:25])=[C:19]([F:27])[CH:18]=1

Participants

5

Reactant 4

HCID 1049PyridineHCID 21552-AminothiazoleHCID 6344DichloromethaneHCID 27363104-Bromo-2-fluorobenzene-1-sulfonyl chloride

Product 1

HCID 251383534-Bromo-2-fluoro-N-thiazol-2-yl-benzenesulfonamideYield 36%

Procedure

To a solution of 2-aminothiazole (4.51 g, 0.0450 mol) and pyridine (24.26 mL, 0.3000 mol) in methylene chloride (40 mL, 0.6 mol) at 0° C. was added portionwise 4-bromo-2-fluorobenzenesulfonyl chloride (8.2 g, 0.030 mol). The reaction mixture was stirred at room temperature overnight. The reaction mixture was concentrated under reduced pressure, diluted with EtOAc, washed with 1N HCl solution, H2O and brine. The organic phase was dried with anhydrous sodium sulfate, filtered and concentrated to give the crude product that was purified via automated flash chromatography (silica gel, 25% EtOAc in hexanes to 100% EtOAc) to give the product as a light brown solid (3.6 g, 36%).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additiondiluted with EtOAc
  3. washwashed with 1N HCl solution, H2O and brine
  4. dry with materialThe organic phase was dried with anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto give the crude product that
  8. customwas purified

Sources & evidence

ORD record
ord-a7de876b12d84a268667377c93faf3d1
Source dataset
uspto-grants-2012_02
Patent number
US08124610B2

Reaction notes

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