Sodium Carbonate → HCID 23624542, Verbindung

HRID 389044

Reaktionsgleichung

Reaktionsgleichung von HRID 389044
Cl[C:2]1[N:3]=[N:4][C:5]([N:8]2[CH2:13][CH2:12][N:11]([CH:14]3[CH2:16][CH2:15]3)[CH2:10][CH2:9]2)=[CH:6][CH:7]=1.C(=O)([O-])[O-].[Na+].[Na+].[CH2:23]1[O:31][C:30]2[CH:29]=[CH:28][C:27](B(O)O)=[CH:26][C:25]=2[O:24]1>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.C(#N)C>[O:24]1[C:25]2[CH:26]=[CH:27][C:28]([C:2]3[N:3]=[N:4][C:5]([N:8]4[CH2:13][CH2:12][N:11]([CH:14]5[CH2:16][CH2:15]5)[CH2:10][CH2:9]4)=[CH:6][CH:7]=3)=[CH:29][C:30]=2[O:31][CH2:23]1

Komponenten

6

Edukt 3

HCID 10340Sodium CarbonateHCID 2734371(2H-1,3-benzodioxol-5-yl)boronic acidHCID 614441503-Chloro-6-(4-cyclopropylpiperazin-1-yl)pyridazine

Produkt 1

HCID 23624542HCID 23624542, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418476HCID 178418476, VerbindungKatalysatorHCID 6342AcetonitrileLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

3-Chloro-6-(4-cyclopropylpiperazin-1-yl)pyridazine (8.0 g, 33.5 mmol), acetonitrile (100 mL), 1 M sodium carbonate solution (100.5 mL, 100.5 mmol) and bis(triphenylphosphine)palladium(II) chloride (1.17 g, 1.67 mmol) were mixed and degassed in vacuo under nitrogen. 3,4-Methylenedioxybenzeneboronic acid (8.34 g, 50.3 mmol) was added and the mixture was heated to 80° C. for 16 h. The precipitated product was filtered and washed with acetonitrile and water, and dried in vacuo. The solid was suspended in methanol (500 mL) and 2,2 equivalents of a 4M HCl in dioxane solution was added. The formed solution was filtered, concentrated in vacuo and acetonitrile (100 mL) was added. The suspension was stirred for 1 h, filtered and the solid dried in vacuo to yield 3-(1,3-benzodioxol-5-yl)-6-(4-cyclopropylpiperazin-1-yl)pyridazine as a yellow powder, 11.4 g, 86%.

Aufarbeitung

  1. customdegassed in vacuo under nitrogen
  2. filtrationThe precipitated product was filtered
  3. washwashed with acetonitrile and water
  4. customdried in vacuo
  5. addition2,2 equivalents of a 4M HCl in dioxane solution was added
  6. filtrationThe formed solution was filtered
  7. concentrationconcentrated in vacuo and acetonitrile (100 mL)
  8. additionwas added
  9. filtrationfiltered
  10. customthe solid dried in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-98a5652ec5814fc58020b88c343717e9
Quelldatensatz
uspto-grants-2013_02
Patentnummer
US08378097B2

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