Cesium carbonate → 3-Benzyloxy-1-(toluene-4-sulfonylmethyl)-1H-pyridin-2-one

HRID 1716305

Reaktionsgleichung

Reaktionsgleichung von HRID 1716305
[CH2:1]([O:8][C:9]1[C:10](=[O:15])[NH:11][CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([O-])([O-])=O.[Cs+].[Cs+].Cl[CH2:23][S:24]([C:27]1[CH:32]=[CH:31][C:30]([CH3:33])=[CH:29][CH:28]=1)(=[O:26])=[O:25]>CN(C=O)C>[CH2:1]([O:8][C:9]1[C:10](=[O:15])[N:11]([CH2:23][S:24]([C:27]2[CH:32]=[CH:31][C:30]([CH3:33])=[CH:29][CH:28]=2)(=[O:25])=[O:26])[CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

5

Edukt 3

HCID 10796Cesium carbonateHCID 5628451-Chloromethanesulfonyl-4-methylbenzene2×HCID 156664523-(Benzyloxy)pyridin-2-ol

Produkt 1

HCID 685103983-Benzyloxy-1-(toluene-4-sulfonylmethyl)-1H-pyridin-2-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
95 °C

Versuchsvorschrift

To a suspension of 3-benzyloxy-1H-pyridin-2-one (0.22 g, 1.1 mmol) from step A and Cs2CO3 (0.72 g, 2.2 mmol) in dry DMF (5 mL) was added 1-chloromethanesulfonyl-4-methyl-benzene (0.31 g, 1.54 mmol). The reaction mixture was heated at 95° C. overnight and then additional 1-chloromethanesulfonyl-4-methyl-benzene (0.22 g, 1.1 mmol) was added. The reaction mixture was stirred for another 18 h. After the usual work-up, the crude material was purified by chromatography (silica gel, 40% EtOAc/hexanes) to give the product. MS (EI) 370 (M+H)+.

Aufarbeitung

  1. customAfter the usual work-up, the crude material was purified by chromatography (silica gel, 40% EtOAc/hexanes)
  2. customto give the product

Quellen und Nachweise

ORD-Eintrag
ord-7dbff5dd144842579fd4e28af28285a7
Quelldatensatz
uspto-grants-2010_09
Patentnummer
US07803793B2

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