2-Bromo-1-(4-(difluoromethoxy)phenyl)ethan-1-one → 4-[4-(4-Difluoromethoxy-phenyl)-thiazol-2-yl]-2'-nitro-biphenyl-2-carboxylic acid

HRID 1519261Notes

Reaction equation

HRID 1519261 reaction equation
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][CH:24]([F:36])[O:25][C:26]1[CH:35]=[CH:34][C:29]([C:30](=O)[CH2:31]Br)=[CH:28][CH:27]=1>>[F:23][CH:24]([F:36])[O:25][C:26]1[CH:35]=[CH:34][C:29]([C:30]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:31]=2)=[CH:28][CH:27]=1

Participants

3

Reactant 2

HCID 7034962-Bromo-1-(4-(difluoromethoxy)phenyl)ethan-1-oneHCID 866798322'-Nitro-4-thiocarbamoyl-biphenyl-2-carboxylic acid methyl ester2×

Product 1

HCID 715360794-[4-(4-Difluoromethoxy-phenyl)-thiazol-2-yl]-2'-nitro-biphenyl-2-carboxylic acidYield 61%

Procedure

4-[4-(4-Difluoromethoxy-phenyl)-thiazol-2-yl]-2′-nitro-biphenyl-2-carboxylic acid (180 mg, 61%) was prepared from 2′-nitro-4-thiocarbamoyl-biphenyl-2-carboxylic acid methyl ester (which may be prepared as described for Intermediate 4) and 4-(difluoromethoxy)phenacyl bromide (available from Oakwood Products, Inc.) using the procedure described for the preparation of Example 1. 1H NMR (300 MHz, DMSO-d6) δ 13.15 (s, 1H), 8.57 (d, J=1.9 Hz, 1H), 8.11-8.27 (m, 5H), 7.63-7.81 (m, 2H), 7.41-7.48 (m, 2H), 7.30 (d, J=9.2 Hz, 1H).

Workup

  1. customdescribed for the preparation of Example 1

Sources & evidence

ORD record
ord-aa5ff18e35af467e900db00819b9767d
Source dataset
uspto-grants-2015_07
Patent number
US09073881B2

Reaction notes

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