Sodium Carbonate → 3-(3-Nitropyridin-4-yl)cyclohex-2-enone

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Reaktionsgleichung

CC1(C)C(C)(C)OB([C:9]2[CH2:14][CH2:13][CH2:12][C:11](=[O:15])[CH:10]=2)O1.Cl[C:18]1[CH:23]=[CH:22][N:21]=[CH:20][C:19]=1[N+:24]([O-:26])=[O:25].C([O-])([O-])=O.[Na+].[Na+]>O1CCOCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[N+:24]([C:19]1[CH:20]=[N:21][CH:22]=[CH:23][C:18]=1[C:9]1[CH2:14][CH2:13][CH2:12][C:11](=[O:15])[CH:10]=1)([O-:26])=[O:25]

Komponenten

Reaktionsbedingungen

Temperatur: 120 °C

Versuchsvorschrift

To a solution of 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)cyclohex-2-en-1-one (6.0 g, 27 mmol) and 4-chloro-3-nitropyridine (2.4 g, 15 mmol) in 1,4-dioxane (60 mL), 2.0 N aq. Na2CO3 (12 mL, 24 mmol) and tetrakis(triphenylphosphine)palladium(0) (1.8 g, 1.5 mmol) were added. The reaction mixture was heated at 120° C. for 1 h. The reaction mixture was filtered through diatomaceous earth, which was washed with EtOAc. The filtrate was concentrated under reduced pressure and the residue was purified by silica gel column chromatography (eluting with 10-100% EtOAc in hexanes) to give the sub-title compound as a brown solid (1.97 g, 87%). LCMS calc. for C11H11N2O3 (M+H)+: m/z=219.1. Found: 219.0.

Aufarbeitung

filtrationThe reaction mixture was filtered through diatomaceous earth, which
washwas washed with EtOAc
concentrationThe filtrate was concentrated under reduced pressure
customthe residue was purified by silica gel column chromatography (eluting with 10-100% EtOAc in hexanes)

Quellen und Nachweise

ORD-Eintrag: ord-4416c30fbbca45078ff7baece52e298a
Quelldatensatz: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US09278950B2

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