2'-Nitro-4-thiocarbamoyl-biphenyl-2-carboxylic acid methyl ester → 4-[4-(4-Fluoro-phenyl)-thiazol-2-yl]-2'-nitro-biphenyl-2-carboxylic acid methyl ester

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Reaktionsgleichung

FC1C=CC(C(=O)CBr)=CC=1.[CH3:12][O:13][C:14]([C:16]1[C:17]([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=2[N+:40]([O-:42])=[O:41])=[CH:18][CH:19]=[C:20]([C:22]2[S:23][CH:24]=[C:25]([C:27]3[CH:32]=[CH:31][C:30]([F:33])=[CH:29][CH:28]=3)[N:26]=2)[CH:21]=1)=[O:15].COC(C1C(C2C=CC=CC=2[N+]([O-])=O)=CC=C(C(=S)N)C=1)=O>C(O)C>[CH3:12][O:13][C:14]([C:16]1[C:17]([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=2[N+:40]([O-:42])=[O:41])=[CH:18][CH:19]=[C:20]([C:22]2[S:23][CH:24]=[C:25]([C:27]3[CH:28]=[CH:29][C:30]([F:33])=[CH:31][CH:32]=3)[N:26]=2)[CH:21]=1)=[O:15]

Komponenten

Reaktionsbedingungen

Temperatur: 45 °C

Versuchsvorschrift

4-[4-(4-Fluoro-phenyl)-thiazol-2-yl]-2′-nitro-biphenyl-2-carboxylic acid methyl ester 4-Fluorophenacyl bromide (available from Alfa Aesar; 35 mg, 0.16 mmol) was added to a suspension of 2′-nitro-4-thiocarbamoyl-biphenyl-2-carboxylic acid methyl ester (which may be prepared as described for Intermediate 4; 50 mg, 0.16 mmol) in ethanol (2 mL) and the resulting mixture was stirred at 45° C. for 20 h. The reaction mixture was concentrated to a small volume and cooled. The precipitate was collected by filtration to give 4-[4-(4-fluoro-phenyl)-thiazol-2-yl]-2′-nitro-biphenyl-2-carboxylic acid methyl ester (40 mg) which was used directly in the next step without purification.

Aufarbeitung

concentrationThe reaction mixture was concentrated to a small volume
temperaturecooled
filtrationThe precipitate was collected by filtration

Quellen und Nachweise

ORD-Eintrag: ord-94e822ac3930439782e9bac5ab1fb868
Quelldatensatz: uspto-grants-2015_07
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US09073881B2

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