1,2-Dimethoxyethane → 4-(6-Chloro-4-methyl-pyridin-3-yl)-5-methoxy-10-oxa-tricyclo[5.2.1.02,6]dec-4-en-3-one

HRID 41685

Reaktionsgleichung

I[C:2]1[C:3](=[O:14])[CH:4]2[CH:9]([C:10]=1[O:11][CH3:12])[CH:8]1[O:13][CH:5]2[CH2:6][CH2:7]1.[Cl:15][C:16]1[N:21]=[CH:20][C:19](B(O)O)=[C:18]([CH3:25])[CH:17]=1.COCCOC.C(=O)([O-])[O-].[Na+].[Na+]>Cl.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[Cl:15][C:16]1[N:21]=[CH:20][C:19]([C:2]2[C:3](=[O:14])[CH:4]3[CH:9]([C:10]=2[O:11][CH3:12])[CH:8]2[O:13][CH:5]3[CH2:6][CH2:7]2)=[C:18]([CH3:25])[CH:17]=1

Komponenten

Reaktionsbedingungen

Temperatur: 130 °C

Versuchsvorschrift

A microwave vial is charged with 4-iodo-5-methoxy-10-oxa-tricyclo[5.2.1.0*2,6*]dec-4-en-3-one (184 mg, 0.6 mmol), 6-chloro-4-methylpyridine-3-boronic acid (103 mg, 0.6 mmol) and bis(triphenylphosphine)palladium dichloride (21 mg, 0.03 mmol). DME (1 ml) is added, followed by 2N aqueous sodium carbonate solution (0.6 ml, 1.2 mmol) and the reaction is heated to 130° C. by microwave irradiation, with stirring, for 30 minutes. The reaction is then diluted with 2N HCl (20 ml), extracted with ethyl acetate (20 ml), and the organic layer is removed and purified by flash chromatography on silica gel to give 4-(6-chloro-4-methyl-pyridin-3-yl)-5-methoxy-10-oxa-tricyclo[5.2.1.0*2,6*]dec-4-en-3-one (119 mg).

Aufarbeitung

extractionextracted with ethyl acetate (20 ml)
customthe organic layer is removed
custompurified by flash chromatography on silica gel

Quellen und Nachweise

ORD-Eintrag: ord-7aaa8d583ecf4c4fbab7dc484af1bd7e
Quelldatensatz: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08530667B2

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