Cesium carbonate → 1-(5-Chloro-6-fluoro-2-pyridyl)-6-(6-methylpyrazin-2-yl)pyrazolo[4,3-c]pyridine

HRID 57885Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 57885
[CH3:1][C:2]1[N:7]=[C:6]([C:8]2[N:13]=[CH:12][C:11]3[CH:14]=[N:15][NH:16][C:10]=3[CH:9]=2)[CH:5]=[N:4][CH:3]=1.Br[C:18]1[N:23]=[C:22]([F:24])[C:21]([Cl:25])=[CH:20][CH:19]=1.C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2>O1CCOCC1.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]>[Cl:25][C:21]1[CH:20]=[CH:19][C:18]([N:16]2[C:10]3[CH:9]=[C:8]([C:6]4[CH:5]=[N:4][CH:3]=[C:2]([CH3:1])[N:7]=4)[N:13]=[CH:12][C:11]=3[CH:14]=[N:15]2)=[N:23][C:22]=1[F:24]

Komponenten

7

Edukt 4

HCID 10796Cesium carbonateHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 722139976-Bromo-3-chloro-2-fluoropyridineHCID 867070806-(6-methylpyrazin-2-yl)-1H-pyrazolo[4,3-c]pyridine

Produkt 1

HCID 867070791-(5-Chloro-6-fluoro-2-pyridyl)-6-(6-methylpyrazin-2-yl)pyrazolo[4,3-c]pyridineAusbeute 48,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

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

Reaktionsbedingungen

Temperatur
105 °C

Versuchsvorschrift

To a mixture of 6-(6-methylpyrazin-2-yl)-1H-pyrazolo[4,3-c]pyridine (1.325 mmol; 279.9 mg) and 6-bromo-3-chloro-2-fluoro-pyridine (1.988 mmol; 418.3 mg) in 1,4-Dioxane (10 mL) under Argon was added cesium carbonate (3.975 mmol; 1295 mg), Xantphos (0.2253 mmol; 130.4 mg), and tris(dibenzylideneacetone)dipalladium(0) (0.1325 mmol; 121.3 mg). The resulting mixture was sealed in a pressure tube and heated at 105° C. overnight. The reaction mixture cooled to room temperature, and filtered through Celite. The filter cake was washed with DCM. The filtrate was concentrated. The residue was purified on silica eluted with 0 to 6% MeOH in DCM to afford 1-(5-chloro-6-fluoro-2-pyridyl)-6-(6-methylpyrazin-2-yl)pyrazolo[4,3-c]pyridine (217.1 mg, 48%).

Aufarbeitung

  1. customThe resulting mixture was sealed in a pressure tube
  2. temperatureThe reaction mixture cooled to room temperature
  3. filtrationfiltered through Celite
  4. washThe filter cake was washed with DCM
  5. concentrationThe filtrate was concentrated
  6. customThe residue was purified on silica
  7. washeluted with 0 to 6% MeOH in DCM

Quellen und Nachweise

ORD-Eintrag
ord-6b78e39db4b440cc8bedf00573524ac8
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09434725B2

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