2,4-Dibromo-1,3-thiazole → 2-(4-Bromothiazol-2-yloxy)pyridine

HRID 1893715Notes

Reaction equation

HRID 1893715 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[OH:7].Br[C:9]1[S:10][CH:11]=[C:12]([Br:14])[N:13]=1>CN(C=O)C.C(=O)([O-])[O-].[Ag+2]>[Br:14][C:12]1[N:13]=[C:9]([O:7][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=2)[S:10][CH:11]=1

Participants

5

Reactant 2

HCID 27632972,4-Dibromo-1,3-thiazoleHCID 178516071HCID 178516071, compound

Product 1

HCID 668718162-(4-Bromothiazol-2-yloxy)pyridineYield 37.9%

Reagents, catalysts & solvents 2

HCID 178418647HCID 178418647, compoundCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
140 °C

Procedure

According to Scheme 3, Step 2: Pyridin-2-ol (4.12 mmol, 0.39 g) and then silver carbonate (4.94 mmol, 1.36 g) were added to a solution of 2,4-dibromothiazole (4.12 mmol, 1.00 g) in DMF (18 mL) and the reaction mixture was heated at 140° C. overnight. After evaporation of the solvent, the reaction mixture was dissolved in DCM and was filtered through celite. The organic phase was washed with water, was dried over MgSO4, was filtered and was concentrated under reduced pressure to yield 2-(4-bromothiazol-2-yloxy)pyridine (1.56 mmol, 400 mg, 34%).

Workup

  1. customAfter evaporation of the solvent
  2. dissolutionthe reaction mixture was dissolved in DCM
  3. filtrationwas filtered through celite
  4. washThe organic phase was washed with water
  5. dry with materialwas dried over MgSO4
  6. filtrationwas filtered
  7. concentrationwas concentrated under reduced pressure

Sources & evidence

ORD record
ord-cc5d29f9b3d94f949fa1c3e43fdc83c4
Source dataset
uspto-grants-2013_08
Patent number
US08513252B2

Reaction notes

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