p-Fluoronitrobenzene → 3-(4-nitrophenyl)[1,3]oxazolo[4,5-b]pyridin-2(3H)-one

HRID 82512Notes

Reaction equation

HRID 82512 reaction equation
[O:1]1[C:9]2[C:4](=[N:5][CH:6]=[CH:7][CH:8]=2)[NH:3][C:2]1=[O:10].[H-].[Na+].F[C:14]1[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[CH:16][CH:15]=1>CN(C=O)C.C(OCC)(=O)C>[N+:20]([C:17]1[CH:18]=[CH:19][C:14]([N:3]2[C:4]3=[N:5][CH:6]=[CH:7][CH:8]=[C:9]3[O:1][C:2]2=[O:10])=[CH:15][CH:16]=1)([O-:22])=[O:21]

Participants

6

Reactant 3

HCID 9590p-FluoronitrobenzeneHCID 24758Sodium hydrideHCID 2799900Oxazolo(4,5-b)pyridin-2(3H)-one

Product 1

HCID 585776343-(4-nitrophenyl)[1,3]oxazolo[4,5-b]pyridin-2(3H)-oneYield 19.3%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of oxazolo[4,5-b]pyridin-2(3H)-one (200 mg) in DMF (3.5 mL) was treated with a 60% dispersion of sodium hydride in mineral oil (62 mg) and the resulting mixture stirred at ambient temperature for 5 min. The mixture was treated with 1-fluoro-4-nitrobenzene (248 mg) then stirred at 100° C. for 17 h. After this time, the reaction mixture was cooled to ambient temperature, diluted with ethyl acetate (100 ml), washed with water (2×50 ml), 5% aqueous lithium chloride (50 mL) then brine (50 mL), dried over sodium sulfate, and filtered and the filtrate was concentrated under reduced pressure. The residue obtained was purified by chromatography (silica, heptane to 1:1 ethyl acetate/heptane) to afford 3-(4-nitrophenyl) [1,3]oxazolo[4,5-b]pyridin-2(3H)-one (73 mg) as a yellow solid.

Workup

  1. stirringthen stirred at 100° C. for 17 h
  2. temperatureAfter this time, the reaction mixture was cooled to ambient temperature
  3. washwashed with water (2×50 ml), 5% aqueous lithium chloride (50 mL)
  4. dry with materialbrine (50 mL), dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationthe filtrate was concentrated under reduced pressure
  7. customThe residue obtained
  8. customwas purified by chromatography (silica, heptane to 1:1 ethyl acetate/heptane)

Sources & evidence

ORD record
ord-8bb1a35fa60040fcb5e07732b8314db1
Source dataset
uspto-grants-2014_09
Patent number
US08846713B2

Reaction notes

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