2-Bromo-4'-(trifluoromethyl)acetophenone → 2'-Nitro-4-[4-(4-trifluoromethyl-phenyl)-thiazol-2-yl]-biphenyl-2-carboxylic acid

HRID 1519265

Reaktionsgleichung

Reaktionsgleichung von HRID 1519265
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:36])([F:35])[C:25]1[CH:34]=[CH:33][C:28]([C:29](=O)[CH2:30]Br)=[CH:27][CH:26]=1>>[N+:20]([C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=1[C:6]1[C:5]([C:3]([OH:2])=[O:4])=[CH:10][C:9]([C:11]2[S:13][CH:30]=[C:29]([C:28]3[CH:33]=[CH:34][C:25]([C:24]([F:23])([F:35])[F:36])=[CH:26][CH:27]=3)[N:12]=2)=[CH:8][CH:7]=1)([O-:22])=[O:21]

Komponenten

3

Edukt 2

HCID 3219792-Bromo-4'-(trifluoromethyl)acetophenoneHCID 866798322'-Nitro-4-thiocarbamoyl-biphenyl-2-carboxylic acid methyl ester2×

Produkt 1

HCID 715363452'-Nitro-4-[4-(4-trifluoromethyl-phenyl)-thiazol-2-yl]-biphenyl-2-carboxylic acidAusbeute 40 %

Versuchsvorschrift

2′-Nitro-4-[4-(4-trifluoromethyl-phenyl)-thiazol-2-yl]-biphenyl-2-carboxylic acid (120 mg, 40%) was prepared from 2′-nitro-4-thiocarbamoyl-biphenyl-2-carboxylic acid methyl ester (which may be prepared as described for Intermediate 4) and 4-(trifluoromethyl)phenacyl bromide (available from Oakwood Products, Inc.) using the procedure described for the preparation of Example 1. 1H NMR (300 MHz, DMSO-d6) δ 13.16 (s, 1H), 8.59 (s, 1H), 8.51 (s, 1H), 8.27-8.31 (m, 3H), 8.15 (d, J=8.1 Hz, 1H), 7.77-7.87 (m, 3H), 7.66 (t, J=8.0 Hz, 1H), 7.42-7.49 (m, 2H).

Aufarbeitung

  1. customdescribed for the preparation of Example 1

Quellen und Nachweise

ORD-Eintrag
ord-e77c0aec3a9d40c2b308b93c4a018d5b
Quelldatensatz
uspto-grants-2015_07
Patentnummer
US09073881B2

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