Bromine → N-{5-[(2-amino[1,3]thiazolo[5,4-b]pyridin-5-yl)oxy]-2-chlorophenyl}-2,2,2-trifluoroacetamide

HRID 2366779Notes

Reaction equation

HRID 2366779 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([O:8][C:9]2[CH:10]=[CH:11][C:12]([Cl:22])=[C:13]([NH:15][C:16](=[O:21])[C:17]([F:20])([F:19])[F:18])[CH:14]=2)=[N:6][CH:7]=1.[S-:23][C:24]#[N:25].[K+].BrBr>C(O)(=O)C>[NH2:25][C:24]1[S:23][C:7]2[C:2]([N:1]=1)=[CH:3][CH:4]=[C:5]([O:8][C:9]1[CH:10]=[CH:11][C:12]([Cl:22])=[C:13]([NH:15][C:16](=[O:21])[C:17]([F:20])([F:18])[F:19])[CH:14]=1)[N:6]=2

Participants

5

Reactant 3

HCID 24408BromineHCID 516872Potassium thiocyanateHCID 57387327N-{5-[(5-aminopyridin-2-yl)oxy]-2-chlorophenyl}-2,2,2-trifluoroacetamide

Product 1

HCID 57384282N-{5-[(2-amino[1,3]thiazolo[5,4-b]pyridin-5-yl)oxy]-2-chlorophenyl}-2,2,2-trifluoroacetamideYield 72%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

N-{5-[(5-Aminopyridin-2-yl)oxy]-2-chlorophenyl}-2,2,2-trifluoroacetamide (12 g, 36.2 mmol) and potassium thiocyanate (14.1 g, 145 mmol) were suspended in acetic acid (145 mL), bromine (8.67 g, 54.3 mmol) was added dropwise under ice-cooling, and the reaction mixture was stirred at room temperature for 16 hr. The reaction mixture was filtered through celite, and the filtrate was concentrated under reduced pressure. The residual oily substance was dissolved in ethyl acetate (100 mL), and aqueous sodium hydrogen carbonate solution (150 mL) was gradually added to partition the solution. The organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residual solid was collected by filtration with diisopropyl ether (100 mL), and dried to give the title compound (10.1 g, 72%) as a pale-yellow solid.

Workup

  1. temperaturecooling
  2. filtrationThe reaction mixture was filtered through celite
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. dissolutionThe residual oily substance was dissolved in ethyl acetate (100 mL)
  5. additionaqueous sodium hydrogen carbonate solution (150 mL) was gradually added
  6. customto partition the solution
  7. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  8. concentrationconcentrated under reduced pressure
  9. filtrationThe residual solid was collected by filtration with diisopropyl ether (100 mL)
  10. customdried

Sources & evidence

ORD record
ord-e01ed5c33dde46fd8480aeefe5fef612
Source dataset
uspto-grants-2014_04
Patent number
US08697874B2

Reaction notes

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