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Water → 6-Fluoro-1-[1-[6-(1-methylpyrazol-4-yl)pyridazin-3-yl]piperidin-4-yl]-2,3-dihydroindole

HRID 512824
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 512824
[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][NH:14][CH2:13][CH2:12]2)=[CH:4][CH:3]=1.Cl[C:18]1[N:19]=[N:20][C:21]([C:24]2[CH:25]=[N:26][N:27]([CH3:29])[CH:28]=2)=[CH:22][CH:23]=1.CCN(C(C)C)C(C)C.O>CS(C)=O>[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:18]3[N:19]=[N:20][C:21]([C:24]4[CH:25]=[N:26][N:27]([CH3:29])[CH:28]=4)=[CH:22][CH:23]=3)[CH2:13][CH2:12]2)=[CH:4][CH:3]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 220383846-Fluoro-1-(piperidin-4-yl)indolineHCID 545956073-Chloro-6-(1-methyl-1H-pyrazol-4-yl)pyridazine

Produkt 1

HCID 715715696-Fluoro-1-[1-[6-(1-methylpyrazol-4-yl)pyridazin-3-yl]piperidin-4-yl]-2,3-dihydroindole

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679
Dimethyl Sulfoxide
Lösungsmittel

Reaktionsbedingungen

Temperatur
180 °C

Versuchsvorschrift

To a mixture of 6-fluoro-1-(piperidin-4-yl)indoline (256 mg, 1 mmol), 3-chloro-6-(1-methyl-1H-pyrazol-4-yl)pyridazine prepared as in STEP 1 above (194 mg, 1.0 mmol) in DMSO (3 mL) was added DIPEA (0.52 mL, 3 mmol). The resulting mixture was sealed and heated at 180° C. for 1.5 h under microwave irradiation. The resulting mixture was poured into H2O (30 mL) and the aqueous layer was extracted with 30% CH2Cl2/Et2O (30 mL×5). The combined organic layer was 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 the title compound, 6-fluoro-1-(1-(6-(1-methyl-1H-pyrazol-4-yl)pyridazin-3-yl)piperidin-4-yl)indoline.

Aufarbeitung

  1. customThe resulting mixture was sealed
  2. extractionthe aqueous layer was extracted with 30% CH2Cl2/Et2O (30 mL×5)
  3. dry with materialThe combined organic layer was dried (Na2SO4)
  4. filtrationfiltered
  5. customThe solvent was removed
  6. customthe resulting residue was purified by column

Quellen und Nachweise

ORD-Eintrag
ord-905ea678004b4b31a7bfdfd05b732f0e
Quelldatensatz
uspto-grants-2015_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09102669B2

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