Tetrahydrofuran → HCID 58926072, compound

HRID 2196172Notes

Reaction equation

Br[C:2]1[C:6]([CH3:8])([CH3:7])[O:5]/[C:4](=[C:9]2/[C:10](=[O:19])[NH:11][C:12]3[C:17]/2=[CH:16][CH:15]=[C:14]([F:18])[CH:13]=3)/[CH:3]=1.[NH:20]1[CH2:25][CH2:24][O:23][CH2:22][CH2:21]1.C1CCN2C(=NCCC2)CC1.C1C[O:40][CH2:39]C1>C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:7][C:6]1([CH3:8])[O:5]/[C:4](=[C:9]2/[C:10](=[O:19])[NH:11][C:12]3[C:17]/2=[CH:16][CH:15]=[C:14]([F:18])[CH:13]=3)/[CH:3]=[C:2]1[C:39]([N:20]1[CH2:25][CH2:24][O:23][CH2:22][CH2:21]1)=[O:40]

Participants

Conditions

Temperature: 108 °C

Procedure

A pressure tube was charged with (3E)-3-(4-bromo-5,5-dimethylfuran-2(5H)-ylidene)-6-fluoro-1,3-dihydro-2H-indol-2-one (60 mg, 0.19 mmol), morpholine (48 mg, 0.56 mmol), Mo(CO)6 (49 mg, 0.19 mmol), palladium(II) acetate (4.0 mg, 0.018 mmol), DBU (85 mg, 0.56 mmol) and anhydrous THF (3 mL). The tube was immediately capped under nitrogen and heated in 108° C. bath for 1 hour. After cooling, the reaction mixture was filtered through a short celite pad. The filtrate was concentrated and purified by silica gel flash chromatography (5-10% MeOH in CHCl3) to give (3E)-3-[5,5-dimethyl-4-(morpholin-4-ylcarbonyl)furan-2(5H)-ylidene]-6-fluoro-1,3-dihydro-2H-indol-2-one as a yellow solid. Yield: 39 mg, 55%.

Workup

customThe tube was immediately capped under nitrogen
temperatureAfter cooling
filtrationthe reaction mixture was filtered through a short celite pad
concentrationThe filtrate was concentrated
custompurified by silica gel flash chromatography (5-10% MeOH in CHCl3)

Sources & evidence

ORD record: ord-46557ab09f80441da99f7f0a1c3d27a7
Source dataset: uspto-grants-2012_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08338415B2

Reaction notes

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