Ethyl Acetate → 5-(Furan-2-yl)-7-aza-oxindole

HRID 2213307Notes

Reaction equation

HRID 2213307 reaction equation
Br[C:2]1[CH:3]=[C:4]2[CH2:10][C:9](=[O:11])[NH:8][C:5]2=[N:6][CH:7]=1.[CH3:12][CH2:13][O:14][C:15]([CH3:17])=O>O.[Cl-].C([N+](CC)(CC)CC)C.C(#N)C.[F-].[K+]>[O:14]1[CH:15]=[CH:17][CH:12]=[C:13]1[C:2]1[CH:3]=[C:4]2[CH2:10][C:9](=[O:11])[NH:8][C:5]2=[N:6][CH:7]=1

Participants

6

Reactant 2

HCID 8857Ethyl AcetateHCID 155040625-bromo-1H,2H,3H-pyrrolo(2,3-b)pyridin-2-one

Product 1

HCID 155040685-(Furan-2-yl)-7-aza-oxindole

Reagents, catalysts & solvents 3

HCID 16211205Tetraethylammonium chloride monohydrateCatalystHCID 6342AcetonitrileSolventHCID 522689Potassium FluorideSolvent

Conditions

Temperature
85 °C

Procedure

5-Bromo-1,3-dihydro-2H-pyrrolo[2,3-b]pyridin-2-one (0.75 g, 3.52 mmol), 2-tributyltinfuran (1.26 g, 3.52 mmol), tetraethylammonium chloride hydrate (1.94 g, 10.6 mmol) were combined and dissolved in acetonitrile (10 mL) at room temperature under an atmosphere of nitrogen. Bistriphenylphosphine dichloropalladium (II) (0.25 g, 0.35 mmol) was added, and the reaction was warmed to 85° C. for 16 hours. The reaction was cooled to room temperature and diluted with aqueous KF (10%, 60 mL). This was stirred for 20 minutes and then diluted with EtOAc (60 mL). The biphasic system was passed through celite, the layers separated, and the volatiles removed in vacuo. The resulting residue was triturated with diethyl ether, and the solids were collected by filtration to afford the title compound as a light yelow solid (0.28 g, 36% yield). 1H NMR 300 MHz (DMSO-d6): δ 11.18 (bs, 1H); 8.45 (s, 1H); 7.92 (s, 1H); 7.79 (s, 1H); 6.95 (d, 1H); 6.60 (d, 1H); 3.64 (s, 2H). APCI m/z 201 (M+1).

Workup

  1. temperatureThe reaction was cooled to room temperature
  2. customthe layers separated
  3. customthe volatiles removed in vacuo
  4. customThe resulting residue was triturated with diethyl ether
  5. filtrationthe solids were collected by filtration

Sources & evidence

ORD record
ord-b1eee9a38aa2405b8c0496e862285081
Source dataset
uspto-grants-2006_09
Patent number
US07105529B2

Reaction notes

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