Trifluoroacetic anhydride → HCID 58478791, compound

HRID 1011338Notes

Reaction equation

HRID 1011338 reaction equation
[CH3:1][C:2]1[N+:7]([O-])=[C:6]2[CH2:9][O:10][C:11](=[O:12])[C:5]2=[CH:4][CH:3]=1.FC(F)(F)C(OC(=O)C(F)(F)F)=[O:16]>ClCCl>[OH:16][CH2:1][C:2]1[N:7]=[C:6]2[CH2:9][O:10][C:11](=[O:12])[C:5]2=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 9845Trifluoroacetic anhydrideHCID 67314368HCID 67314368, compound

Product 1

HCID 58478791HCID 58478791, compoundYield 57.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 2-methyl-7H-furo[3,4-b]pyridin-5-one N-oxide (122 mg, 0.74 mmol) in dichloromethane (2 mL) is heated at reflux. Trifluoroacetic anhydride (1.5 mL, 10 mmol) is added dropwise and heating is continued for approximately 30 min. The reaction mixture is cooled and concentrated. The residue is treated with methanol (3 mL) and triethylamine (2 mL) and stirred until no starting material remained. The reaction mixture is concentrated and the residue is purified by chromatography (silica gel). The product containing fractions are concentrated to give the title compound (70 mg, 42%).

Workup

  1. temperatureat reflux
  2. temperatureheating
  3. temperatureThe reaction mixture is cooled
  4. concentrationconcentrated
  5. additionThe residue is treated with methanol (3 mL) and triethylamine (2 mL)
  6. concentrationThe reaction mixture is concentrated
  7. customthe residue is purified by chromatography (silica gel)
  8. additionThe product containing fractions
  9. concentrationare concentrated

Sources & evidence

ORD record
ord-e28a1d04c6804074a0036250ab475997
Source dataset
uspto-grants-2011_07
Patent number
US07977351B2

Reaction notes

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