Cesium carbonate → HCID 86682737, Verbindung

HRID 1755386Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1755386
Br[C:2]1[C:3]2[N:4]([CH:9]=[CH:10][N:11]=2)[N:5]=[C:6]([Cl:8])[CH:7]=1.[C:12]([CH:16]1[CH2:20][CH2:19][N:18]([C:21]2[N:26]=[C:25]([NH2:27])[CH:24]=[CH:23][CH:22]=2)[CH2:17]1)([CH3:15])([CH3:14])[CH3:13].C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1.C([O-])([O-])=O.[Cs+].[Cs+]>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].O1CCOCC1>[C:12]([CH:16]1[CH2:20][CH2:19][N:18]([C:21]2[N:26]=[C:25]([NH:27][C:2]3[C:3]4[N:4]([CH:9]=[CH:10][N:11]=4)[N:5]=[C:6]([Cl:8])[CH:7]=3)[CH:24]=[CH:23][CH:22]=2)[CH2:17]1)([CH3:15])([CH3:13])[CH3:14]

Komponenten

7

Edukt 4

HCID 10796Cesium carbonateHCID 634876Binap, (A+-)-HCID 468352698-Bromo-6-chloroimidazo(1,2-b)pyridazineHCID 86682736HCID 86682736, Verbindung

Produkt 1

HCID 86682737HCID 86682737, VerbindungAusbeute 43,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

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

Versuchsvorschrift

A mixture of 8-bromo-6-chloroimidazo[1,2-b]pyridazine (573 mg, 2.47 mmol), 6-(3-tert-butylpyrrolidin-1-yl)pyridin-2-amine (540 mg, 2.47 mmol), Pd2(dba)3 (142 mg, 0.25 mmol), BINAP (307 mg, 0.50 mmol), Cs2CO3 (2.4 g, 7.41 mmol) and dioxane (20 mL) was heated to reflux with stirring for 15 h under N2. The solvent was removed in vacuo and the resulting mixture was purified by chromatography (silica gel, 200-300 mesh, dichloromethane:MeOH=50:1) to give N-(6-(3-tert-butylpyrrolidin-1-yl)pyridin-2-yl)-6-chloroimidazo[1,2-b]pyridazin-8-amine (400 mg, crude) as a brown oil. LC-MS: [M+H]+, 371.1, tR=2.23 min.

Aufarbeitung

  1. temperaturewas heated
  2. temperatureto reflux
  3. customThe solvent was removed in vacuo
  4. customthe resulting mixture was purified by chromatography (silica gel, 200-300 mesh, dichloromethane:MeOH=50:1)

Quellen und Nachweise

ORD-Eintrag
ord-cdc012ac554543f7af7cc5bd9077e1a7
Quelldatensatz
uspto-grants-2015_10
Patentnummer
US09169259B2

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