Pyridine → 4-Isopropyl-N-[4-(1-propionyl-azetidin-3-yl)-phenyl]-benzenesulfonamide

HRID 1260236Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1260236
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH:10]2[CH2:13][N:12]([C:14](=[O:17])[CH2:15][CH3:16])[CH2:11]2)=[CH:6][CH:5]=1)([O-])=O.O.O.Cl[Sn]Cl.NC1C=CC=CC=1.N1C=CC=CC=1.[CH:36]([C:39]1[CH:44]=[CH:43][C:42]([S:45](Cl)(=[O:47])=[O:46])=[CH:41][CH:40]=1)([CH3:38])[CH3:37]>CCO.C(Cl)Cl>[CH:36]([C:39]1[CH:44]=[CH:43][C:42]([S:45]([NH:1][C:4]2[CH:9]=[CH:8][C:7]([CH:10]3[CH2:13][N:12]([C:14](=[O:17])[CH2:15][CH3:16])[CH2:11]3)=[CH:6][CH:5]=2)(=[O:47])=[O:46])=[CH:41][CH:40]=1)([CH3:38])[CH3:37]

Komponenten

8

Edukt 5

HCID 1049PyridineHCID 6115AnilineHCID 61436Stannous chloride dihydrateHCID 27348824-(Propan-2-yl)benzene-1-sulfonyl chlorideHCID 574700801-(3-(4-Nitrophenyl)azetidin-1-yl)propan-1-one

Produkt 1

HCID 536286634-Isopropyl-N-[4-(1-propionyl-azetidin-3-yl)-phenyl]-benzenesulfonamideAusbeute 36 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Following the same procedure as described in 46.5, 1-[3-(4-nitro-phenyl)-azetidin-1-yl]-propan-1-one (480 mg, 2.04 mmol) in EtOH (20 ml) was treated with SnCl2.2H2O (2.25 g, 9.97 mmol) and half of the resulting aniline in CH2Cl2 (15 ml) was then treated with pyridine (140 μl, 1.71 mmol) and 4-isopropyl-benzensulfonylchloride (230 μl, 1.28 mmol). Purification of the crude product by flash column chromatography (heptane:ethyl acetate, 1:1) provided the title compound (140 mg, 36% for two steps) as a pale yellow gum.

Aufarbeitung

  1. customPurification of the crude product by flash column chromatography (heptane:ethyl acetate, 1:1)

Quellen und Nachweise

ORD-Eintrag
ord-8f99cf9fff5442c8ba1b821246b36df5
Quelldatensatz
uspto-grants-2013_06
Patentnummer
US08470810B2

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