6-Chloro-1-(6-fluoropyridin-2-yl)-1H-pyrazolo[4,3-c]pyridine → 6-(6-Ethylpyrazin-2-yl)-1-(6-fluoro-2-pyridyl)pyrazolo[4,3-c]pyridine

HRID 57856

Reaktionsgleichung

Reaktionsgleichung von HRID 57856
Cl[C:2]1[N:7]=[CH:6][C:5]2[CH:8]=[N:9][N:10]([C:11]3[CH:16]=[CH:15][CH:14]=[C:13]([F:17])[N:12]=3)[C:4]=2[CH:3]=1.[CH2:18]([C:20]1[N:25]=[C:24]([Sn](C)(C)C)[CH:23]=[N:22][CH:21]=1)[CH3:19]>CN(C)C(=O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH2:18]([C:20]1[N:25]=[C:24]([C:2]2[N:7]=[CH:6][C:5]3[CH:8]=[N:9][N:10]([C:11]4[CH:16]=[CH:15][CH:14]=[C:13]([F:17])[N:12]=4)[C:4]=3[CH:3]=2)[CH:23]=[N:22][CH:21]=1)[CH3:19]

Komponenten

5

Edukt 2

HCID 862802436-Chloro-1-(6-fluoropyridin-2-yl)-1H-pyrazolo[4,3-c]pyridineHCID 86707055(6-Ethylpyrazin-2-yl)-trimethyl-stannane

Produkt 1

HCID 867070546-(6-Ethylpyrazin-2-yl)-1-(6-fluoro-2-pyridyl)pyrazolo[4,3-c]pyridineAusbeute 41,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 31374DimethylacetamideLösungsmittel

Reaktionsbedingungen

Temperatur
150 °C

Versuchsvorschrift

To a solution of 6-chloro-1-(6-fluoro-2-pyridyl)pyrazolo[4,3-c]pyridine (85 mg; 0.34 mmol) and tetrakis(triphenylphosphine)palladium (40 mg, 0.034 mmol) in N,N-dimethylacetamide; 2.0 mL was added (6-ethylpyrazin-2-yl)-trimethyl-stannane (185 mg, 0.684 mmol). The reaction was purged with N2 for 5 min then heated at 150° C. for 45 min in biotage microwave. The reaction mixture was filtered through celite and concentrated. The crude product was diluted with EtOAc then washed with water. The organic layers was dried with sodium sulfate, filtered, and concentrated in vacuum. The crude product was purified by flash chromatography (EtOAc/Heptane eluted at 50% EtOAc) to give 6-(6-ethylpyrazin-2-yl)-1-(6-fluoro-2-pyridyl)pyrazolo[4,3-c]pyridine (45 mg) in 41% yield. MS (ESI) m/z: 321.2

Aufarbeitung

  1. customThe reaction was purged with N2 for 5 min
  2. filtrationThe reaction mixture was filtered through celite
  3. concentrationconcentrated
  4. additionThe crude product was diluted with EtOAc
  5. washthen washed with water
  6. dry with materialThe organic layers was dried with sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuum
  9. customThe crude product was purified by flash chromatography (EtOAc/Heptane eluted at 50% EtOAc)

Quellen und Nachweise

ORD-Eintrag
ord-e906e0df7413481c9589cdf8d984c21b
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09434725B2

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