Water → 6-(Furan-2-yl)-oxindole

HRID 2300287Notes

Reaction equation

HRID 2300287 reaction equation
Br[C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][C:7](=[O:11])[NH:8]2)=[CH:4][CH:3]=1.[OH2:12]>O.[Cl-].C([N+](CC)(CC)CC)C.C(#N)C.[Pd].Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[O:12]1[CH:4]=[CH:3][CH:2]=[C:10]1[C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][C:7](=[O:11])[NH:8]2)=[CH:4][CH:3]=1

Participants

7

Reactant 2

HCID 962WaterHCID 27732896-bromo-2,3-dihydro-1H-indol-2-one

Product 1

HCID 219070396-(Furan-2-yl)-oxindole

Reagents, catalysts & solvents 4

HCID 23938PalladiumCatalystHCID 16211205Tetraethylammonium chloride monohydrateCatalystHCID 178418476HCID 178418476, compoundCatalystHCID 6342AcetonitrileSolvent

Conditions

Temperature
85 °C

Procedure

6-Bromo-oxindole (0.40 g, 1.88 mmol), 2-tributyltinfuran (0.71 mL, 2.26 mmol), and tetraethylammonium chloride hydrate (0.31 g, 1.88 mmol) were combined and dissolved in acetonitrile (15 mL). The palladium catalyst, bistriphenylphosphinedichloropalladium (II) (0.66 g, 0.09 mmol) was added and the reaction was warmed to 85° C. under nitrogen for 20 h. The reaction was cooled to room temperature and diluted with water (15 mL) before passing the mixture through celite. The pad of celite was washed with EtOAc and the filtrates were combined and separated. The aqueous layer was washed with EtOAc (2×20 mL each). The combined organic phases were washed with brine and dried over sodium sulfate. The volatiles ere removed in vacuo. The resulting residue was triturated with diethyl ether and the solid was collected by filtration (0.13 g, 34%). 1H NMR 300 MHz (DMSO-d6) δ 10.5 (s, 1H); 7.75 (s, 1H); 7.30 (m, 2H); 7.11 (s, 1H); 6.91 (m, 1H); 6.60 (m, 1H); 3.52 (s, 2H).

Workup

  1. temperatureThe reaction was cooled to room temperature
  2. washThe pad of celite was washed with EtOAc
  3. customseparated
  4. washThe aqueous layer was washed with EtOAc (2×20 mL each)
  5. washThe combined organic phases were washed with brine
  6. dry with materialdried over sodium sulfate
  7. customThe volatiles ere removed in vacuo
  8. customThe resulting residue was triturated with diethyl ether
  9. filtrationthe solid was collected by filtration (0.13 g, 34%)

Sources & evidence

ORD record
ord-2e7d5e0e5ef945a381091e1a89affb76
Source dataset
uspto-grants-2002_12
Patent number
US06498176B1

Reaction notes

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