3,5-Bis(trifluoromethyl)phenacyl bromide → 4-[4-(3,5-Bis-trifluoromethyl-phenyl)-thiazol-2-yl]-2'-nitro-biphenyl-2-carboxylic acid

HRID 1519266Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1519266
C[O:2][C:3]([C:5]1[C:6]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[N+:20]([O-:22])=[O:21])=[CH:7][CH:8]=[C:9]([C:11](=[S:13])[NH2:12])[CH:10]=1)=[O:4].[F:23][C:24]([F:40])([F:39])[C:25]1[CH:26]=[C:27]([C:35](=O)[CH2:36]Br)[CH:28]=[C:29]([C:31]([F:34])([F:33])[F:32])[CH:30]=1>>[F:23][C:24]([F:39])([F:40])[C:25]1[CH:26]=[C:27]([C:35]2[N:12]=[C:11]([C:9]3[CH:10]=[C:5]([C:3]([OH:2])=[O:4])[C:6]([C:14]4[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=4[N+:20]([O-:22])=[O:21])=[CH:7][CH:8]=3)[S:13][CH:36]=2)[CH:28]=[C:29]([C:31]([F:32])([F:33])[F:34])[CH:30]=1

Komponenten

3

Edukt 2

HCID 27361703,5-Bis(trifluoromethyl)phenacyl bromideHCID 866798322'-Nitro-4-thiocarbamoyl-biphenyl-2-carboxylic acid methyl ester2×

Produkt 1

HCID 866798414-[4-(3,5-Bis-trifluoromethyl-phenyl)-thiazol-2-yl]-2'-nitro-biphenyl-2-carboxylic acidAusbeute 32 %

Versuchsvorschrift

4-[4-(3,5-Bis-trifluoromethyl-phenyl)-thiazol-2-yl]-2′-nitro-biphenyl-2-carboxylic acid (110 mg, 32%) was prepared from 2′-nitro-4-thiocarbamoyl-biphenyl-2-carboxylic acid methyl ester (which may be prepared as described for Intermediate 4) and 3′,5′-bis(trifluoromethyl)-2-bromoacetophenone (available from Oakwood Products, Inc.) using the procedure described for the preparation of Example 1. 1H NMR (300 MHz, DMSO-d6) δ 13.20 (s, 1H), 8.79 (s, 1H), 8.72 (s, 2H), 8.55 (s, 1H), 8.32 (d, J=8.1 Hz, 1H), 8.12-8.17 (m, 2H), 7.79 (t, J=7.6 Hz, 1H), 7.66 (t, J=7.6 Hz, 1H), 7.41-7.50 (m, 2H).

Aufarbeitung

  1. customdescribed for the preparation of Example 1

Quellen und Nachweise

ORD-Eintrag
ord-0838410ec997444399f3d24bd2855694
Quelldatensatz
uspto-grants-2015_07
Patentnummer
US09073881B2

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