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

HRID 2300282Notes

Reaction equation

HRID 2300282 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:8](=[N:9][CH:10]=1)[NH:7][C:6](=[O:11])[CH2:5]2.[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[C:8](=[N:9][CH:10]=1)[NH:7][C:6](=[O:11])[CH2:5]2

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-oxindoleYield 36%

Reagents, catalysts & solvents 3

HCID 16211205Tetraethylammonium chloride monohydrateCatalystHCID 6342AcetonitrileSolventHCID 522689Potassium FluorideSolvent

Conditions

Temperature
85 °C

Procedure

5-Bromo-7-azaoxindole (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 h. 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 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-0d7a96a357ff4a2f9b30aeb5de299e66
Source dataset
uspto-grants-2002_12
Patent number
US06498176B1

Reaction notes

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