Potassium Carbonate → (4-Chloro-2-fluorophenyl)(6-chloro-2-methyl-8-(morpholinomethyl)imidazo[1,2-b]pyridazin-3-yl)methanone

HRID 597859Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 597859
[NH2:1][CH2:2][C:3]1[C:4]2[N:5]([C:10]([C:14]([C:16]3[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][C:17]=3[F:23])=[O:15])=[C:11]([CH3:13])[N:12]=2)[N:6]=[C:7]([Cl:9])[CH:8]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:31][CH2:32][O:33][CH2:34][CH2:35]Br>O>[Cl:22][C:19]1[CH:20]=[CH:21][C:16]([C:14]([C:10]2[N:5]3[N:6]=[C:7]([Cl:9])[CH:8]=[C:3]([CH2:2][N:1]4[CH2:35][CH2:34][O:33][CH2:32][CH2:31]4)[C:4]3=[N:12][C:11]=2[CH3:13])=[O:15])=[C:17]([F:23])[CH:18]=1

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 21521Bis(2-bromoethyl) etherHCID 86642486(8-(Aminomethyl)-6-chloro-2-methylimidazo[1,2-b]pyridazin-3-yl)(4-chloro-2-fluorophenyl)methanone

Produkt 1

HCID 56954584(4-Chloro-2-fluorophenyl)(6-chloro-2-methyl-8-(morpholinomethyl)imidazo[1,2-b]pyridazin-3-yl)methanoneAusbeute 31 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

Combine (8-(aminomethyl)-6-chloro-2-methylimidazo[1,2-b]pyridazin-3-yl)(4-chloro-2-fluorophenyl)methanone (1.15 g, 3.3 mmol), water (12 mL), potassium carbonate (495 mg, 1.1 equiv.), and 2-bromoethyl ether (0.47 mL, 1.1 equiv) in a 20 mL microwave reaction vessel. Seal with a crimp cap then heat in a microwave reactor at 120° C. for 20 min. Cool to RT and partition between EA and water. Wash EA layer with aqueous saturated sodium chloride, and dry over anhydrous magnesium sulfate. Filter and concentrate in vacuo. Purify on silica gel (4:1 hexane:EA→2:1 hexane:EA→1:1 hexane:EA) to give the title compound (0.43 g, 31%) as a light yellow foam. LCMS (4 min)=423.0, 425.0, M+1.

Aufarbeitung

  1. customSeal with a crimp
  2. customcap
  3. temperatureCool to RT
  4. custompartition between EA and water
  5. dry with materialWash EA layer with aqueous saturated sodium chloride, and dry over anhydrous magnesium sulfate
  6. filtrationFilter
  7. concentrationconcentrate in vacuo
  8. customPurify on silica gel (4:1 hexane

Quellen und Nachweise

ORD-Eintrag
ord-c2bd167adc814fdfa0ba855d89d559f3
Quelldatensatz
uspto-grants-2011_03
Patentnummer
US07897600B2

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