Borane;tetrahydrofuran → 4-Isopropyl-N-[6-(1-propyl-azetidin-3-yl)-pyridin-3-yl]-benzenesulfonamide

HRID 2262617Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2262617
[CH:1]([C:4]1[CH:9]=[CH:8][C:7]([S:10]([NH:13][C:14]2[CH:15]=[N:16][C:17]([CH:20]3[CH2:23][N:22]([C:24](=O)[CH2:25][CH3:26])[CH2:21]3)=[CH:18][CH:19]=2)(=[O:12])=[O:11])=[CH:6][CH:5]=1)([CH3:3])[CH3:2].B.C1COCC1>C1COCC1>[CH:1]([C:4]1[CH:9]=[CH:8][C:7]([S:10]([NH:13][C:14]2[CH:15]=[N:16][C:17]([CH:20]3[CH2:23][N:22]([CH2:24][CH2:25][CH3:26])[CH2:21]3)=[CH:18][CH:19]=2)(=[O:11])=[O:12])=[CH:6][CH:5]=1)([CH3:3])[CH3:2]

Komponenten

4

Edukt 2

HCID 2723981Borane;tetrahydrofuranHCID 53628661HCID 53628661, Verbindung

Produkt 1

HCID 536286604-Isopropyl-N-[6-(1-propyl-azetidin-3-yl)-pyridin-3-yl]-benzenesulfonamideAusbeute 66,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of 4-isopropyl-N-[6-(1-propionyl-azetidin-3-yl)-pyridin-3-yl]-benzenesulfonamide (150 mg, 0.38 mmol) in THF (15 ml) was added dropwise 1M BH3.THF (3.8 ml) and the mixture was stirred at room temperature for 12 h. It was then quenched by careful addition of 1N aqueous HCl (10 ml) and the resulting solution was heated at reflux for 4 h. The solution was next cooled to room temperature, adjusted to pH˜8 with 2 N NaOH solution and diluted with CH2Cl2. Separation of the layers, drying (Na2SO4) of the organic phase, filtration and evaporation in vacuo provided the crude material, which was purified by flash column chromatography (CH2Cl2:methanol, 95:5) to give the title compound (95 mg, 66%) as a light yellow oil.

Aufarbeitung

  1. customIt was then quenched by careful addition of 1N aqueous HCl (10 ml)
  2. temperaturethe resulting solution was heated
  3. temperatureat reflux for 4 h
  4. temperaturenext cooled to room temperature
  5. additiondiluted with CH2Cl2
  6. customSeparation of the layers
  7. customdrying
  8. filtration(Na2SO4) of the organic phase, filtration and evaporation in vacuo
  9. customprovided the crude material, which
  10. customwas purified by flash column chromatography (CH2Cl2:methanol, 95:5)

Quellen und Nachweise

ORD-Eintrag
ord-6cfdb300404f43d5b39ca41edfc27498
Quelldatensatz
uspto-grants-2010_12
Patentnummer
US07851463B2

Notizen zur Reaktion

Wird geladen…