Trifluoroacetic anhydride → 6-(3-Nitrophenoxy)imidazo[1,2-a]pyridin-2-amine

HRID 1874398Notes

Reaction equation

HRID 1874398 reaction equation
CC1C=CC(S([NH:11][CH:12]2[CH:17]=[CH:16][C:15]([O:18][C:19]3[CH:24]=[CH:23][CH:22]=[C:21]([N+:25]([O-:27])=[O:26])[CH:20]=3)=[CH:14][N:13]2[CH2:28][C:29]([NH2:31])=O)(=O)=O)=CC=1.FC(F)(F)C(OC(=O)C(F)(F)F)=O>ClCCl>[N+:25]([C:21]1[CH:20]=[C:19]([CH:24]=[CH:23][CH:22]=1)[O:18][C:15]1[CH:16]=[CH:17][C:12]2[N:13]([CH:28]=[C:29]([NH2:31])[N:11]=2)[CH:14]=1)([O-:27])=[O:26]

Participants

4

Reactant 2

HCID 9845Trifluoroacetic anhydrideHCID 689889522-[2-{[(4-methylphenyl)sulfonyl]amino}-5-(3-nitrophenoxy)pyridin-1(2H)-yl]acetamide

Product 1

HCID 577492806-(3-Nitrophenoxy)imidazo[1,2-a]pyridin-2-amineYield 49%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 2-[2-{[(4-methylphenyl)sulfonyl]amino}-5-(3-nitrophenoxy)pyridin-1(2H)-yl]acetamide (4.70 g, 10.6 mmol), trifluoroacetic anhydride (30 mL) and dichloromethane (40 mL) was stirred at room temperature for 5 hr. The reaction solution was concentrated under reduced pressure, saturated aqueous sodium hydrogen carbonate solution was added to the residue and the mixture was extracted with ethyl acetate (×3). The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate and filtrated. The filtrate was concentrated under reduced pressure, 8N aqueous sodium hydroxide solution (10 mL) and ethanol (30 mL) were added to the residue and the mixture was stirred at room temperature for 15 hr. The reaction mixture was diluted with water and extracted with ethyl acetate (×3). The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate and filtrated. The filtrate was concentrated under reduced pressure, and the residue was purified by column chromatography (silica gel, ethyl acetate) to give the title compound (1.40 g, 49%) as a white solid.

Workup

  1. concentrationThe reaction solution was concentrated under reduced pressure, saturated aqueous sodium hydrogen carbonate solution
  2. additionwas added to the residue
  3. extractionthe mixture was extracted with ethyl acetate (×3)
  4. washThe organic layer was washed with saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltrated
  7. concentrationThe filtrate was concentrated under reduced pressure, 8N aqueous sodium hydroxide solution (10 mL) and ethanol (30 mL)
  8. additionwere added to the residue
  9. stirringthe mixture was stirred at room temperature for 15 hr
  10. additionThe reaction mixture was diluted with water
  11. extractionextracted with ethyl acetate (×3)
  12. washThe organic layer was washed with saturated brine
  13. dry with materialdried over anhydrous magnesium sulfate
  14. filtrationfiltrated
  15. concentrationThe filtrate was concentrated under reduced pressure
  16. customthe residue was purified by column chromatography (silica gel, ethyl acetate)

Sources & evidence

ORD record
ord-162bd7cba75c4d75ac8214ddc05b54b5
Source dataset
uspto-grants-2012_11
Patent number
US08304557B2

Reaction notes

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