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

HRID 2415083Notes

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

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 yellow solid (0.28 g, 36% yield). 1H NMR 300 MHz (DMSO-d6) δ11.18 (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

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

Sources & evidence

ORD record: ord-5f0bec2529d248a09a8fb119096442d3
Source dataset: uspto-grants-2004_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06818632B2

Reaction notes

Loading…