Ammonia → 2-(3-ethylsulfanyl-pyridin-2-yl)-1-methyl-5-pentafluoroethyl-1H-benzimidazole

HRID 530916

Reaktionsgleichung

[CH2:1]([S:3][C:4]1[C:5]([C:10]2[N:14]([CH3:15])[C:13]3[CH:16]=[CH:17][C:18](I)=[CH:19][C:12]=3[N:11]=2)=[N:6][CH:7]=[CH:8][CH:9]=1)[CH3:2].[F:21][C:22]([F:30])([F:29])[C:23]([F:28])([F:27])C([O-])=O.[Na+].C(=O)([O-])O.[Na+].N>[Cu](I)I.C1(C)C(C)=CC=CC=1.CN1C(=O)CCC1>[CH2:1]([S:3][C:4]1[C:5]([C:10]2[N:14]([CH3:15])[C:13]3[CH:16]=[CH:17][C:18]([C:23]([F:28])([F:27])[C:22]([F:30])([F:29])[F:21])=[CH:19][C:12]=3[N:11]=2)=[N:6][CH:7]=[CH:8][CH:9]=1)[CH3:2]

Komponenten

Reaktionsbedingungen

Temperatur: 160 °C

Versuchsvorschrift

A mixture of 2-(3-ethylsulfanyl-pyridin-2-yl)-5-iodo-1-methyl-1H-benzimidazole (340 mg), copper iodide (410 mg), sodium pentafluoropropionate (800 mg), NMP (5 ml), and xylene (5 ml) was stirred at 160° C. for 5 hours. The reaction mixture was allowed to cool to room temperature, and then saturated aqueous sodium hydrogen carbonate solution and 26% ammonia solution were poured thereto. Then, the mixture was extracted with t-butylmethyl ether. The organic layer was dried over sodium sulfate, and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to give 2-(3-ethylsulfanyl-pyridin-2-yl)-1-methyl-5-pentafluoroethyl-1H-benzimidazole (240 mg), which is hereinafter referred to as “the present compound 26”.

Aufarbeitung

temperatureto cool to room temperature
extractionThen, the mixture was extracted with t-butylmethyl ether
dry with materialThe organic layer was dried over sodium sulfate
concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag: ord-4111157bdfd448fe9cf728f8942e8202
Quelldatensatz: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US09353110B2

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