Tetrabutylammonium Fluoride → 8-bromo-2-chloro-4-fluoro-10H-chromeno[3,2-b]pyridin-10-one

HRID 335862Notes

Reaction equation

HRID 335862 reaction equation
[Br:1][C:2]1[CH:15]=[CH:14][C:13]2[O:12][C:11]3[C:6](=[N:7][C:8]([Cl:19])=[CH:9][C:10]=3[N+]([O-])=O)[C:5](=[O:20])[C:4]=2[CH:3]=1.[F-:21].C([N+](CCCC)(CCCC)CCCC)CCC>CN(C=O)C>[Br:1][C:2]1[CH:15]=[CH:14][C:13]2[O:12][C:11]3[C:6](=[N:7][C:8]([Cl:19])=[CH:9][C:10]=3[F:21])[C:5](=[O:20])[C:4]=2[CH:3]=1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 866584708-bromo-2-chloro-4-nitro-10H-chromeno[3,2-b]pyridin-10-one

Product 1

HCID 866584718-bromo-2-chloro-4-fluoro-10H-chromeno[3,2-b]pyridin-10-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 8-bromo-2-chloro-4-nitro-10H-chromeno[3,2-b]pyridin-10-one (80 mg, 0.225 mmol) in 0.8 mL of DMF at 0° C. was added tetrabutylammonium fluoride (1M in THF, 0.45 mL, 0.450 mmol) dropwise. After 15 minutes, the reaction was quenched with saturated NH4Cl (20 mL) and extracted with ethyl acetate (2×10 mL). The combined organics were dried over sodium sulfate, filtered and evaporated to dryness. Purification of the crude residue by column chromatography (SiO2, CH2Cl2 to CH2Cl2/EA=100:3) gave 8-bromo-2-chloro-4-fluoro-10H-chromeno[3,2-b]pyridin-10-one as an off white solid.

Workup

  1. customthe reaction was quenched with saturated NH4Cl (20 mL)
  2. extractionextracted with ethyl acetate (2×10 mL)
  3. dry with materialThe combined organics were dried over sodium sulfate
  4. filtrationfiltered
  5. customevaporated to dryness
  6. customPurification of the crude residue by column chromatography (SiO2, CH2Cl2 to CH2Cl2/EA=100:3)

Sources & evidence

ORD record
ord-214df60280fe44faa9045bdf4bc0fff2
Source dataset
uspto-grants-2014_11
Patent number
US08883782B2

Reaction notes

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