Water → (6-Phenylimidazo[1,2-b]pyridazin-3-yl)(quinolin-6-yl)methanone

HRID 1513782

Reaktionsgleichung

Reaktionsgleichung von HRID 1513782
Cl[C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([C:11]([C:13]3[CH:14]=[C:15]4[C:20](=[CH:21][CH:22]=3)[N:19]=[CH:18][CH:17]=[CH:16]4)=[O:12])=[CH:9][N:10]=2)[N:7]=1.[C:23]1(B(O)O)[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.C(=O)([O-])[O-].[Cs+].[Cs+].O1CCOCC1.O>>[C:23]1([C:2]2[CH:3]=[CH:4][C:5]3[N:6]([C:8]([C:11]([C:13]4[CH:14]=[C:15]5[C:20](=[CH:21][CH:22]=4)[N:19]=[CH:18][CH:17]=[CH:16]5)=[O:12])=[CH:9][N:10]=3)[N:7]=2)[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Komponenten

6

Edukt 5

HCID 962WaterHCID 10796Cesium carbonateHCID 312751,4-DioxaneHCID 66827Phenylboronic AcidHCID 86630275(6-Chloroimidazo[1,2-b]pyridazin-3-yl)(quinolin-6-yl)methanone

Produkt 1

HCID 67502844(6-Phenylimidazo[1,2-b]pyridazin-3-yl)(quinolin-6-yl)methanone

Versuchsvorschrift

A 48 mL sealed tube was charged with (6-chloroimidazo[1,2-b]pyridazin-3-yl)(quinolin-6-yl)methanone (0.530 g, 1.72 mmol), phenylboronic acid (0.314 g, 2.58 mmol), cesium carbonate (1.68 g, 5.15 mmol), PdCl2(dppt)-CH2Cl2 adduct (0.0701 g, 0.0858 mmol), 1,4-dioxane (6.31 ml, 73.8 mmol), and water (1.11 ml, 61.8 mmol), flushed with argon, sealed, then placed in an 80° C. oil bath for 8 hours. The mixture was concentrated then triturated with water, followed by MeOH/DCM to give (6-phenylimidazo[1,2-b]pyridazin-3-yl)(quinolin-6-yl)methanone as a reddish brown solid.

Aufarbeitung

  1. customA 48 mL sealed tube
  2. customflushed with argon
  3. customsealed
  4. customplaced in an 80° C.
  5. customfor 8 hours
  6. concentrationThe mixture was concentrated
  7. customthen triturated with water

Quellen und Nachweise

ORD-Eintrag
ord-d67b5afecaba494a9c612622defd58f1
Quelldatensatz
uspto-grants-2012_07
Patentnummer
US08217177B2

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