4-Methoxystyrene → 1,3-dihydro-4-[(E)-2-(4-methoxyphenyl)-ethenyl]-(Z)-3-[(1H-pyrrol-2-yl)methlene]-2H-indol-2-one

HRID 428713

Reaktionsgleichung

I[C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1/[C:4](=[CH:12]/[C:13]1[NH:14][CH:15]=[CH:16][CH:17]=1)/[C:5](=[O:11])[NH:6]2.[CH3:18][O:19][C:20]1[CH:27]=[CH:26][C:23]([CH:24]=[CH2:25])=[CH:22][CH:21]=1.C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C>CN(C=O)C.CC([O-])=O.CC([O-])=O.[Pd+2]>[CH3:18][O:19][C:20]1[CH:27]=[CH:26][C:23]([CH:24]=[CH:25][C:2]2[CH:10]=[CH:9][CH:8]=[C:7]3[C:3]=2/[C:4](=[CH:12]/[C:13]2[NH:14][CH:15]=[CH:16][CH:17]=2)/[C:5](=[O:11])[NH:6]3)=[CH:22][CH:21]=1

Komponenten

Reaktionsbedingungen

Temperatur: 85 °C

Versuchsvorschrift

To a stirred solution of (Z)-1,3-dihydro-4-iodo-3-[(1H-pyrrol-2-yl)methylene]-2H-indol-2-one (from Example 71 above) (100 mg, 0.29 mmol) in DMF (3 mL) and TEA (2 mL) was added p-methoxy-styrene (79 mg, 0.58 mmol) (from Step A above), tri-o-tolylphosphine (107 mg, 0.35 mmol) (Aldrich) and Pd(OAc)2 (20 mg, 0.089 mmol) (Aldrich). The reaction mixture was stirred at 85° C. overnight in a pressure tube. The solvent was removed in vacuo, and the residue was purified by silica gel chromatography (Hex:EtOAc=5:1) to provide 1,3-dihydro-4-[(E)-2-(4-methoxyphenyl)-ethenyl]-(Z)-3-[(1H-pyrrol-2-yl)methlene]-2H-indol-2-one as a yellow solid. (Yield 72 mg, 73%).

Aufarbeitung

customThe solvent was removed in vacuo
customthe residue was purified by silica gel chromatography (Hex:EtOAc=5:1)

Quellen und Nachweise

ORD-Eintrag: ord-185084d56b5a4fb7842ca64db2aa8737
Quelldatensatz: uspto-grants-2001_11
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US06313310B1

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