Tetrahydrofuran → 1-(1-(6-(1-(2-ethoxyethyl)-1H-pyrazol-4-yl)pyridazin-3-yl)piperidin-4-yl)-6-fluoroindoline

HRID 512849Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 512849
[NH:1]1[CH:5]=[C:4]([C:6]2[N:11]=[N:10][C:9]([N:12]3[CH2:17][CH2:16][CH:15]([N:18]4[C:26]5[C:21](=[CH:22][CH:23]=[C:24]([F:27])[CH:25]=5)[CH2:20][CH2:19]4)[CH2:14][CH2:13]3)=[CH:8][CH:7]=2)[CH:3]=[N:2]1.[CH2:28]([O:30][CH2:31][CH2:32]Br)[CH3:29].C1COCC1.[H-].[Na+]>CCOCC.O.CN(C=O)C>[CH2:28]([O:30][CH2:31][CH2:32][N:1]1[CH:5]=[C:4]([C:6]2[N:11]=[N:10][C:9]([N:12]3[CH2:17][CH2:16][CH:15]([N:18]4[C:26]5[C:21](=[CH:22][CH:23]=[C:24]([F:27])[CH:25]=5)[CH2:20][CH2:19]4)[CH2:14][CH2:13]3)=[CH:8][CH:7]=2)[CH:3]=[N:2]1)[CH3:29]

Komponenten

7

Edukt 4

HCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 611412-Bromoethyl ethyl etherHCID 896139441-(1-(6-(1H-pyrazol-4-yl)pyridazin-3-yl)piperidin-4-yl)-6-fluoroindoline

Produkt 1

HCID 763111101-(1-(6-(1-(2-ethoxyethyl)-1H-pyrazol-4-yl)pyridazin-3-yl)piperidin-4-yl)-6-fluoroindoline

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 21584184Diethylether waterLösungsmittel

Versuchsvorschrift

To a mixture of 1-(1-(6-(1H-pyrazol-4-yl)pyridazin-3-yl)piperidin-4-yl)-6-fluoroindoline (55 mg, 0.15 mmol, 1.0 equiv) and 2-ethoxyethylbromide (0.17 mL, 1.5 mmol, 10 equiv) was added THF (2 mL) and DMF (0.5 mL). NaH (30 mg, 60% in mineral oil, 0.75 mmol, 5 equiv) was then added. The resulting mixture was stirred at room temperature for 1.5 h and then poured into Et2O/H2O (20 mL/20 mL). The organic layer was washed with brine (20 mL), dried (Na2SO4), and filtered. The solvent was removed and the resulting residue was purified by column using 90-100% EtOAc/hexane as the eluent to yield 1-(1-(6-(1-(2-ethoxyethyl)-1H-pyrazol-4-yl)pyridazin-3-yl)piperidin-4-yl)-6-fluoroindoline.

Aufarbeitung

  1. washThe organic layer was washed with brine (20 mL)
  2. dry with materialdried (Na2SO4)
  3. filtrationfiltered
  4. customThe solvent was removed
  5. customthe resulting residue was purified by column

Quellen und Nachweise

ORD-Eintrag
ord-0d17f6b4a32c499f882eb99c70bb1555
Quelldatensatz
uspto-grants-2015_08
Patentnummer
US09102669B2

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