Cesium carbonate → 6-Chloro-4-(5-(methoxymethyl)-1-methyl-1H-pyrazol-3-ylamino)-2-methylpyridazin-3(2H)-one

HRID 1918955Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1918955
BrC1C=C([NH:10][C:11]2[CH:15]=[C:14]([CH2:16][O:17][CH3:18])[N:13]([CH3:19])[N:12]=2)C(=O)N(C)C=1.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.Br[C:63]1[C:64](=[O:71])[N:65]([CH3:70])[N:66]=[C:67]([Cl:69])[CH:68]=1.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]>[Cl:69][C:67]1[CH:68]=[C:63]([NH:10][C:11]2[CH:15]=[C:14]([CH2:16][O:17][CH3:18])[N:13]([CH3:19])[N:12]=2)[C:64](=[O:71])[N:65]([CH3:70])[N:66]=1

Komponenten

7

Edukt 4

HCID 10796Cesium carbonateHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 580441025-Bromo-3-(5-(methoxymethyl)-1-methyl-1H-pyrazol-3-ylamino)-1-methylpyridin-2(1H)-oneHCID 592164744-Bromo-6-chloro-2-methyl-2,3-dihydropyridazin-3-one

Produkt 1

HCID 580438316-Chloro-4-(5-(methoxymethyl)-1-methyl-1H-pyrazol-3-ylamino)-2-methylpyridazin-3(2H)-oneAusbeute 94 %

Reagenzien, Katalysatoren, Lösungsmittel 2

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

Versuchsvorschrift

A mixture of 5-(methoxymethyl)-1-methyl-1H-pyrazol-3-amine 176b (600 mg, 4.26 mmol), XantPhos (300 mg, 0.51 mmol), Pd2 dba3 (310 mg, 0.34 mmol), 4-bromo-6-chloro-2-methylpyridazin-3(2H)-one (103e) (1.22 g, 5.53 mmol) and Cs2CO3 (4.2 g. 12.8 mmol) in 1,4-dioxane (40 mL) was heated at reflux for 2 h. After the completion of the reaction, the mixture was filtered off and washed with methanol (100 mL). The filtrate was evaporated in vacuo and the residue was purified on reverse phase Combi-flash to give 187a (1.13 g, 94%). MS: [M+H]+ 284.

Aufarbeitung

  1. temperaturewas heated
  2. temperatureat reflux for 2 h
  3. customAfter the completion of the reaction
  4. filtrationthe mixture was filtered off
  5. washwashed with methanol (100 mL)
  6. customThe filtrate was evaporated in vacuo
  7. customthe residue was purified on reverse phase Combi-flash

Quellen und Nachweise

ORD-Eintrag
ord-d9c3a43ab6a3499ea1d3bc559952f5d4
Quelldatensatz
uspto-grants-2013_12
Patentnummer
US08618107B2

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