StartseiteMCPWorkbenchSkills
StartseiteWorkbenchBenachrichtigungenMein Bereich
llms.txt · MCP-AnleitungDatenschutz · Nutzungsbedingungen · Supportv1.8.0
  1. Startseite
  2. /Reaktion

Cesium carbonate → 1,1-Dimethyl-3-(4-((2-methyl-6-nitropyridin-3-yl)oxy)pyridin-2-yl)urea

HRID 626521
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 626521
Cl[C:2]1[CH:7]=[C:6]([O:8][C:9]2[C:10]([CH3:18])=[N:11][C:12]([N+:15]([O-:17])=[O:16])=[CH:13][CH:14]=2)[CH:5]=[CH:4][N:3]=1.[CH3:19][N:20]([CH3:24])[C:21]([NH2:23])=[O:22].CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2.C([O-])([O-])=O.[Cs+].[Cs+]>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]>[CH3:19][N:20]([CH3:24])[C:21]([NH:23][C:2]1[CH:7]=[C:6]([O:8][C:9]2[C:10]([CH3:18])=[N:11][C:12]([N+:15]([O-:17])=[O:16])=[CH:13][CH:14]=2)[CH:5]=[CH:4][N:3]=1)=[O:22]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 10796Cesium carbonateHCID 11737N,N-DimethylureaHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 904036213-((2-Chloropyridin-4-yl)oxy)-2-methyl-6-nitropyridine

Produkt 1

HCID 904098671,1-Dimethyl-3-(4-((2-methyl-6-nitropyridin-3-yl)oxy)pyridin-2-yl)ureaAusbeute 86 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 9811564Bis(dibenzylideneacetone)palladiumKatalysatorHCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

A solution of Example A3 (0.500 g, 1.882 mmol) in dioxane (10 mL) was sparged with Ar, treated with N,N-dimethylurea (0.829 g, 9.41 mmol), XANTPHOS (218 mg, 0.376 mmol), and Cs2CO3 (1.226 g, 3.76 mmol), sparged with Ar, treated with Pd2(dba)3 (0.172 g, 0.188 mmol), sparged again with Ar and heated at 100° C. overnight. The mixture was cooled to RT and diluted with EtOAc. The solids were removed via filtration through diatomaceous earth and washed with EtOAc. The filtrates were concentrated to dryness and purified via silica gel chromatography (MeOH/EtOAc) to afford 1,1-dimethyl-3-(4-((2-methyl-6-nitropyridin-3-yl)oxy)pyridin-2-yl)urea (511 mg, 86%). 1H NMR (400 MHz, DMSO-d6): δ 9.05 (s, 1H), 8.25-8.19 (m, 2H), 7.82 (d, J=8.7 Hz, 1H), 7.50 (d, J=2.3 Hz, 1H), 6.71 (dd, J=5.7, 2.4 Hz, 1H), 2.89 (s, 6H), 2.73 (s, 3H); MS (ESI) m/z: 318.1 (M+H+).

Aufarbeitung

  1. customsparged with Ar
  2. customsparged again with Ar
  3. temperatureThe mixture was cooled to RT
  4. additiondiluted with EtOAc
  5. customThe solids were removed via filtration through diatomaceous earth
  6. washwashed with EtOAc
  7. concentrationThe filtrates were concentrated to dryness
  8. custompurified via silica gel chromatography (MeOH/EtOAc)

Quellen und Nachweise

ORD-Eintrag
ord-4e2e563dfe204e9ea28940588b325941
Quelldatensatz
uspto-grants-2016_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09309224B2

Notizen zur Reaktion

Wird geladen…

Auf dieser SeiteKomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion