Water → HCID 90417307, compound

HRID 588265Notes

Reaction equation

HRID 588265 reaction equation
[N:1]([CH2:4][C:5]([C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][CH:15]=1)[NH:12][C:11](=[O:16])[CH2:10]2)=[O:6])=[N+]=[N-].[C:17](Cl)(=O)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.CCN(C(C)C)C(C)C.O>CN(C=O)C.[Pd].CCOC(C)=O>[C:18]1([C:17]2[O:6][C:5]([C:7]3[CH:8]=[C:9]4[C:13](=[CH:14][CH:15]=3)[NH:12][C:11](=[O:16])[CH2:10]4)=[CH:4][N:1]=2)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

8

Reactant 4

HCID 962WaterHCID 7412Benzoyl chlorideHCID 81531DiisopropylethylamineHCID 90418124HCID 90418124, compound

Product 1

HCID 90417307HCID 90417307, compoundYield 24%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 5-(2-azidoacetyl)indolin-2-one (0.20 g, 1.1 mmol) in DMF (5 ml) was added 10% Pd—C (0.20 g), and the mixture was stirred for 3.5 h at room temperature under H2 atmosphere. The mixture was passed through Celite. To the filtrate was added benzoyl chloride (0.12 ml, 1.1 mmol) and iPr2NEt (0.36 ml, 2.2 mmol), and the reaction mixture was stirred for 1 h at 0° C. H2O and EtOAc were added to the mixture, and insoluble solid was removed by filtration. The filtrate was separated and the organic layer was washed with H2O and brine, dried over Na2SO4 and evaporated. The residue was dissolved in sulfuric acid (2.0 ml) and the mixture was heated for 2 h at 90° C. The mixture was cooled to room temperature, and H2O was added. The mixture was extracted with EtOAc, washed with H2O and brine, dried over Na2SO4 and evaporated. Purification by column chromatography (EtOAc/hex) gave 5-(2-phenyloxazol-5-yl)indolin-2-one (0.07 g, 24%).

Workup

  1. stirringthe reaction mixture was stirred for 1 h at 0° C
  2. customwas removed by filtration
  3. customThe filtrate was separated
  4. washthe organic layer was washed with H2O and brine
  5. dry with materialdried over Na2SO4
  6. customevaporated
  7. dissolutionThe residue was dissolved in sulfuric acid (2.0 ml)
  8. temperaturethe mixture was heated for 2 h at 90° C
  9. temperatureThe mixture was cooled to room temperature
  10. additionH2O was added
  11. extractionThe mixture was extracted with EtOAc
  12. washwashed with H2O and brine
  13. dry with materialdried over Na2SO4
  14. customevaporated
  15. customPurification by column chromatography (EtOAc/hex)

Sources & evidence

ORD record
ord-298306e98fc04186ad53b41bd10edd85
Source dataset
uspto-grants-2016_01
Patent number
US09227962B2

Reaction notes

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