Trifluoroacetic anhydride → HCID 118599030, compound

HRID 1050343Notes

Reaction equation

HRID 1050343 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([F:14])[C:5]([C:9]([O:11][CH2:12][CH3:13])=[O:10])=[N+:6]([O-])[CH:7]=1.FC(F)(F)C(OC(=O)C(F)(F)F)=[O:18]>CN(C)C=O>[Br:1][C:2]1[C:7](=[O:18])[NH:6][C:5]([C:9]([O:11][CH2:12][CH3:13])=[O:10])=[C:4]([F:14])[CH:3]=1

Participants

4

Reactant 2

HCID 9845Trifluoroacetic anhydrideHCID 118598963HCID 118598963, compound

Product 1

HCID 118599030HCID 118599030, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

To a stirred solution of ethyl 5-bromo-3-fluoro-1-oxido-pyridin-1-ium-2-carboxylate (3, 0.85 g, 3.21 mmol) in dimethylformamide (15 mL) was added trifluoroacetic anhydride (1.35 g, 6.42 mmol) at 0° C. The reaction mixture was warmed to 50° C. and stirred for 1 h, quenched with saturated aqueous sodium bicarbonate solution and extracted with dichloromethane (2×100 mL). The organic layers were separated, dried with magnesium sulfate, filtered and concentrated to dryness under vacuum to afford ethyl 5-bromo-3-fluoro-6-oxo-1H-pyridine-2-carboxylate (4) as a yellow solid. Yield: 0.8 g, 94%; MS (ESI) m/z 264 [M+1]+; 1H NMR (400 MHz, DMSO-d6) δ 7.86 (m, 1H), 4.47 (q, J=7.2 Hz, 2H), 1.43 (t, J=7.2 Hz, 3H).

Workup

  1. customquenched with saturated aqueous sodium bicarbonate solution
  2. extractionextracted with dichloromethane (2×100 mL)
  3. customThe organic layers were separated
  4. dry with materialdried with magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated to dryness under vacuum

Sources & evidence

ORD record
ord-0a0e21fb953c4fe898bf0b6f9600d547
Source dataset
uspto-grants-2016_07
Patent number
US09382248B2

Reaction notes

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