Cesium carbonate → 2-([1,2,4]Triazolo[4,3-a]pyridin-3-yl)-6,8-difluoroquinoline

HRID 876472Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 876472
Cl[C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[C:5]([F:13])[CH:6]=[C:7]([F:12])[CH:8]=2)[N:3]=1.[N:14]1[N:15]=[CH:16][N:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=12.C([O-])([O-])=O.[Cs+].[Cs+]>O1CCOCC1.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>[N:14]1[N:15]=[C:16]([C:2]2[CH:11]=[CH:10][C:9]3[C:4](=[C:5]([F:13])[CH:6]=[C:7]([F:12])[CH:8]=3)[N:3]=2)[N:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=12

Komponenten

6

Edukt 3

HCID 10796Cesium carbonateHCID 249770[1,2,4]Triazolo[4,3-a]pyridineHCID 642093072-Chloro-6,8-difluoroquinoline

Produkt 1

HCID 672304752-([1,2,4]Triazolo[4,3-a]pyridin-3-yl)-6,8-difluoroquinolineAusbeute 59,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418476HCID 178418476, VerbindungKatalysatorHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

2-Chloro-6,8-difluoroquinoline (0.025 g, 0.125 mmol) was combined with [1,2,4]triazolo[4,3-a]pyridine (0.016 g, 0.14 mmol), micronized Cs2CO3 (0.082 g, 0.25 mmol), and PdCl2(PPh3)2 (0.0088 g, 0.013 mmol), and the solids were slurried in dioxane (1.25 mL). The reaction was degassed with argon (bubbled through the solution) then heated to reflux for 20 hours. The crude reaction mixture was chromatographed without workup on SiO2 eluting with a gradient of 6% NH4OH in MeOH/ethyl acetate to provide the desired product as an orange solid (21 mg).

Aufarbeitung

  1. customThe reaction was degassed with argon (
  2. custombubbled through the solution)
  3. temperaturethen heated
  4. temperatureto reflux for 20 hours
  5. customThe crude reaction mixture
  6. customwas chromatographed without workup on SiO2 eluting with a gradient of 6% NH4OH in MeOH/ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-7794335bce9347b0bdf0fb3bfe10d4ab
Quelldatensatz
uspto-grants-2015_03
Patentnummer
US08987251B2

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