Trifluoroacetic anhydride → 8-bromo-10-oxo-10H-chromeno[3,2-b]pyridine 1-oxide

HRID 529418Notes

Reaction equation

HRID 529418 reaction equation
[Br:1][C:2]1[CH:15]=[CH:14][C:13]2[O:12][C:11]3[C:6](=[N:7][CH:8]=[CH:9][CH:10]=3)[C:5](=[O:16])[C:4]=2[CH:3]=1.C(N)(N)=[O:18].OO.FC(F)(F)C(OC(=O)C(F)(F)F)=O>C(Cl)Cl>[Br:1][C:2]1[CH:15]=[CH:14][C:13]2[O:12][C:11]3[C:6](=[N+:7]([O-:18])[CH:8]=[CH:9][CH:10]=3)[C:5](=[O:16])[C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 9845Trifluoroacetic anhydrideHCID 31294Carbamide PeroxideHCID 584662358-bromo-10H-chromeno[3,2-b]pyridin-10-one

Product 1

HCID 667282008-bromo-10-oxo-10H-chromeno[3,2-b]pyridine 1-oxide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 8-bromo-10H-chromeno[3,2-b]pyridin-10-one (60 g, 217 mmol) and urea peroxide (42.9 g, 456 mmol) in 120 mL of DCM at 0° C. was added dropwise trifluoroacetic anhydride (63.9 mL, 456 mmol). The resulting reaction was stirred for 2 h. The reaction was quenched with 10% Na2S2O3, extracted with DCM, dried over Na2SO4 and evaporated to dryness to give crude 8-bromo-10-oxo-10H-chromeno[3,2-b]pyridine 1-oxide as a pale yellow solid.

Workup

  1. customThe resulting reaction
  2. customThe reaction was quenched with 10% Na2S2O3
  3. extractionextracted with DCM
  4. dry with materialdried over Na2SO4
  5. customevaporated to dryness

Sources & evidence

ORD record
ord-2982795fd26242b4af0c032d73a23ad8
Source dataset
uspto-grants-2016_05
Patent number
US09346827B2

Reaction notes

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