2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → 6-fluoro-1-(1-(6-(1-methyl-1H-pyrazol-4-yl)pyridazin-3-yl)piperidin-4-yl)-1H-indole

HRID 512837Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 512837
[F:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][CH2:7][N:8]2[CH:11]2[CH2:16][CH2:15][N:14]([C:17]3[N:18]=[N:19][C:20]([C:23]4[CH:24]=[N:25][N:26]([CH3:28])[CH:27]=4)=[CH:21][CH:22]=3)[CH2:13][CH2:12]2)=[CH:4][CH:3]=1.C(C1C(=O)C(Cl)=C(Cl)C(=O)C=1C#N)#N.CCOC(C)=O>C1COCC1>[F:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[CH:7][N:8]2[CH:11]2[CH2:16][CH2:15][N:14]([C:17]3[N:18]=[N:19][C:20]([C:23]4[CH:24]=[N:25][N:26]([CH3:28])[CH:27]=4)=[CH:21][CH:22]=3)[CH2:13][CH2:12]2)=[CH:4][CH:3]=1

Komponenten

5

Edukt 3

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 8857Ethyl AcetateHCID 715715696-Fluoro-1-[1-[6-(1-methylpyrazol-4-yl)pyridazin-3-yl]piperidin-4-yl]-2,3-dihydroindole

Produkt 1

HCID 715852956-fluoro-1-(1-(6-(1-methyl-1H-pyrazol-4-yl)pyridazin-3-yl)piperidin-4-yl)-1H-indole

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of 6-fluoro-1-(1-(6-(1-methyl-1H-pyrazol-4-yl)pyridazin-3-yl)piperidin-4-yl)indoline (75 mg, 0.2 mmol) in THF (3 mL) was added DDQ (54 mg, 0.24 mmol). The resulting mixture was stirred at room temperature for 30 min and was poured into EtOAc (30 mL). The organic layer washed with Na2CO3(aq) (30 mL), H2O (30 mL), dried (Na2SO4), and filtered. The solvent was removed and the resulting residue purified by column using 80-90-100% EtOAc/(CH2Cl2/hexane=1/1) as the eluent to yield 6-fluoro-1-(1-(6-(1-methyl-1H-pyrazol-4-yl)pyridazin-3-yl)piperidin-4-yl)-1H-indole, which was then converted to its corresponding HCl salt.

Aufarbeitung

  1. washThe organic layer washed with Na2CO3(aq) (30 mL), H2O (30 mL)
  2. dry with materialdried (Na2SO4)
  3. filtrationfiltered
  4. customThe solvent was removed
  5. customthe resulting residue purified by column

Quellen und Nachweise

ORD-Eintrag
ord-66a671102de949ac93c5c54a2924daed
Quelldatensatz
uspto-grants-2015_08
Patentnummer
US09102669B2

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