Sodium Carbonate → 6-Chloro-3-(2-chloro-pyridin-4-yl)-imidazo[1,2-a]pyridine

HRID 383312Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 383312
Br[C:2]1[N:6]2[CH:7]=[C:8]([Cl:11])[CH:9]=[CH:10][C:5]2=[N:4][CH:3]=1.[Cl:12][C:13]1[CH:18]=[C:17](B(O)O)[CH:16]=[CH:15][N:14]=1.C([O-])([O-])=O.[Na+].[Na+]>O1CCOCC1.O.C1(C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)[Pd][P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[Cl:11][C:8]1[CH:9]=[CH:10][C:5]2[N:6]([C:2]([C:17]3[CH:16]=[CH:15][N:14]=[C:13]([Cl:12])[CH:18]=3)=[CH:3][N:4]=2)[CH:7]=1

Komponenten

7

Edukt 3

HCID 10340Sodium CarbonateHCID 51515952-Chloropyridine-4-boronic acidHCID 457900423-Bromo-6-chloroimidazo[1,2-a]pyridine

Produkt 1

HCID 866443446-Chloro-3-(2-chloro-pyridin-4-yl)-imidazo[1,2-a]pyridine

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178419050HCID 178419050, VerbindungKatalysatorHCID 962WaterLösungsmittel2×HCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

To a solution of 3-bromo-6-chloro-imidazo[1,2-a]pyridine (1 eq, 18.1 mmol, 4.2 g), 2-chloropyridin-4-yl boronic acid (1.05 eq, 19 mmol, 3 g), Na2CO3 (2 eq, 36.2 mmol, 3.84 g) in dioxane (30 ml) and water (10 ml), under an inert atmosphere of argon is added bis(triphenylphosphine)palladium II chloride (1.23 g). The reaction mixture is heated at 100° C. for 16 hours. The mixture is diluted with H2O (50 ml) and extracted with EtOAc. The combined organic portions are washed with brine, dried (MgSO4) and concentrated in vacuo. The residue is purified by flash chromatography on silica eluting with 0-50% EtOAc in iso-hexane to afford the title compound; [M+H]+=264 (266).

Aufarbeitung

  1. extractionextracted with EtOAc
  2. washThe combined organic portions are washed with brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated in vacuo
  5. customThe residue is purified by flash chromatography on silica eluting with 0-50% EtOAc in iso-hexane

Quellen und Nachweise

ORD-Eintrag
ord-ca169e7cd1ac457d8b4a67956b0cf0f8
Quelldatensatz
uspto-grants-2013_02
Patentnummer
US08367662B2

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