4-Toluenesulfonyl chloride → N-(3-((3-bromopyridin-2-yl)oxy)cyclobutyl)-4-methylbenzenesulfonamide
Reaktionsgleichung
Cl.[Br:2][C:3]1[C:4]([O:9][CH:10]2[CH2:13][CH:12]([NH2:14])[CH2:11]2)=[N:5][CH:6]=[CH:7][CH:8]=1.CCN(CC)CC.[C:22]1([CH3:32])[CH:27]=[CH:26][C:25]([S:28](Cl)(=[O:30])=[O:29])=[CH:24][CH:23]=1>C(Cl)Cl>[Br:2][C:3]1[C:4]([O:9][CH:10]2[CH2:11][CH:12]([NH:14][S:28]([C:25]3[CH:26]=[CH:27][C:22]([CH3:32])=[CH:23][CH:24]=3)(=[O:30])=[O:29])[CH2:13]2)=[N:5][CH:6]=[CH:7][CH:8]=1Komponenten
Edukt 3
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 0 °C
Versuchsvorschrift
To a solution of 3-((3-bromopyridin-2-yl)oxy)cyclobutanamine hydrochloride (243 mg, 1 mmol) in dry DCM (10 mL) was added Et3N (1 mL). The reaction mixture was cooled to 0° C. with an ice bath, and p-toluenesulfonyl chloride (380 mg, 2 mmol) was added dropwise. After 1 hour, the reaction mixture was warmed to room temperature, and stirred overnight. Then the reaction mixture was washed with brine, dried over Na2SO4, filtered, and concentrated under vacuum to give the crude product. The crude product was purified by flash chromatography on silica gel (20% to 45% EtOAc in petroleum ether) to give N-(3-((3-bromopyridin-2-yl)oxy)cyclobutyl)-4-methylbenzenesulfonamide (318 mg, 0.8 mmol, yield 80%). ESI-MS (M+1): 397 calc. for C16H17BrN2O3S 396.
Aufarbeitung
- temperaturethe reaction mixture was warmed to room temperature
- washThen the reaction mixture was washed with brine
- dry with materialdried over Na2SO4
- filtrationfiltered
- concentrationconcentrated under vacuum
- customto give the crude product
- customThe crude product was purified by flash chromatography on silica gel (20% to 45% EtOAc in petroleum ether)
Quellen und Nachweise
- ORD-Eintrag
- ord-053c23eb0d5049eaab7e5ff52856f1e7
- Quelldatensatz
- uspto-grants-2015_02
- Patentnummer
- US08952037B2
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