1-Bromo-3-chloropropane → 6-(3-Chloropropoxy)-5-(2,4-difluorophenoxy)-1-isobutyl-1H-indazole

HRID 1897472

Reaktionsgleichung

[F:1][C:2]1[CH:22]=[C:21]([F:23])[CH:20]=[CH:19][C:3]=1[O:4][C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][C:13]=1[OH:14])[N:10]([CH2:15][CH:16]([CH3:18])[CH3:17])[N:9]=[CH:8]2.C([O-])([O-])=O.[Cs+].[Cs+].Br[CH2:31][CH2:32][CH2:33][Cl:34]>CN(C=O)C.O.CCOCC>[Cl:34][CH2:33][CH2:32][CH2:31][O:14][C:13]1[CH:12]=[C:11]2[C:7]([CH:8]=[N:9][N:10]2[CH2:15][CH:16]([CH3:18])[CH3:17])=[CH:6][C:5]=1[O:4][C:3]1[CH:19]=[CH:20][C:21]([F:23])=[CH:22][C:2]=1[F:1]

Komponenten

Reaktionsbedingungen

Temperatur: 80 °C

Versuchsvorschrift

To a solution of 5-(2,4-difluorophenoxy)-1-isobutyl-1H-indazol-6-ol (0.015 g, 0.05 mmol) in DMF (1 mL) was added Cs2CO3. The reaction mixture was stirred for 30 minutes before the addition of 1-bromo-3-chloropropane (0.01 g, 0.08 mmol) and then was heated to 80° C. for 25 hours. After cooling the mixture to room temperature, the reaction mixture was diluted with water and ether and the layers separated. The aqueous layer was extracted with ether and the combined organic layers were washed with 1N NaOH, water, and brine. The crude mixture was dried over Na2SO4 and concentrated under reduced pressure to afford the product with a small impurity. The crude mixture was used in the next reaction without further purification.

Aufarbeitung

temperatureAfter cooling the mixture to room temperature
customthe layers separated
extractionThe aqueous layer was extracted with ether
washthe combined organic layers were washed with 1N NaOH, water, and brine
dry with materialThe crude mixture was dried over Na2SO4
concentrationconcentrated under reduced pressure
customto afford the product with a small impurity

Quellen und Nachweise

ORD-Eintrag: ord-fffee2b82dfd42d9b41cf7503a029eb1
Quelldatensatz: uspto-grants-2013_08
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08518983B2

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