Acetamide → N-(4-((6-nitropyridin-3-yl)oxy)pyridin-2-yl)acetamide

HRID 626496

Reaktionsgleichung

Cl[C:2]1[CH:7]=[C:6]([O:8][C:9]2[CH:10]=[N:11][C:12]([N+:15]([O-:17])=[O:16])=[CH:13][CH:14]=2)[CH:5]=[CH:4][N:3]=1.[C:18]([NH2:21])(=[O:20])[CH3:19].C([O-])([O-])=O.[Cs+].[Cs+].CCOC(C)=O>O1CCOCC1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].CC(C1C=C(C(C)C)C(C2C=CC=CC=2P(C2CCCCC2)C2CCCCC2)=C(C(C)C)C=1)C>[N+:15]([C:12]1[N:11]=[CH:10][C:9]([O:8][C:6]2[CH:5]=[CH:4][N:3]=[C:2]([NH:21][C:18](=[O:20])[CH3:19])[CH:7]=2)=[CH:14][CH:13]=1)([O-:17])=[O:16]

Komponenten

Reaktionsbedingungen

Temperatur: 80 °C

Versuchsvorschrift

A degassed solution of Example A1 (2.0 g, 7.95 mmol) in dioxane (30 mL) added treated with acetamide (1.878 g, 31.8 mmol), Cs2CO3 (2.59 g, 7.95 mmol), X-Phos (0.189 g, 0.397 mmol), and Pd2(dba)3 (0.364 g, 0.397 mmol) and heated at 80° C. for 16 h. The mixture was cooled to RT, treated with EtOAc, the solids removed via filtration through diatomaceous earth and rinsed well with EtOAc. The filtrate was washed with water, then brine, dried over Na2SO4, concentrated to dryness and purified via silica gel chromatography (EtOAc/Hex) to afford N-(4-((6-nitropyridin-3-yl)oxy)pyridin-2-yl)acetamide (1.48 g, 68%). MS (ESI) m/z: 275.1 (M+H+).

Aufarbeitung

temperatureThe mixture was cooled to RT
customthe solids removed via filtration through diatomaceous earth
washrinsed well with EtOAc
washThe filtrate was washed with water
dry with materialbrine, dried over Na2SO4
concentrationconcentrated to dryness
custompurified via silica gel chromatography (EtOAc/Hex)

Quellen und Nachweise

ORD-Eintrag: ord-b3c4a19b1b1e40a3bb8d496342721504
Quelldatensatz: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US09309224B2

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