2-Bromo-1-(3,5-difluorophenyl)ethanone → HCID 86679843, compound

HRID 1519278Notes

Reaction equation

HRID 1519278 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][C:24]1[CH:25]=[C:26]([CH:31]=[C:32]([F:34])[CH:33]=1)[C:27](=O)[CH2:28]Br>>[F:23][C:24]1[CH:25]=[C:26]([C:27]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:28]=2)[CH:31]=[C:32]([F:34])[CH:33]=1

Participants

3

Reactant 2

HCID 27783312-Bromo-1-(3,5-difluorophenyl)ethanoneHCID 866798322'-Nitro-4-thiocarbamoyl-biphenyl-2-carboxylic acid methyl ester2×

Product 1

HCID 86679843HCID 86679843, compoundYield 14%

Procedure

4-[4-(3,5-Difluoro-phenyl)-thiazol-2-yl]-2′-nitro-biphenyl-2-carboxylic acid (38 mg, 14%) 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-difluorophenacyl bromide (available from SynQuest Laboratories, Inc.) using the procedure described for the preparation of Example 18. 1H NMR (300 MHz, DMSO-d6) δ 8.41-8.50 (m, 2H), 8.03 (d, J=8.1 Hz, 2H), 7.79 (d, J=7.2 Hz, 2H), 7.50-7.68 (m, 2H), 7.21-7.33 (m, 3H).

Workup

  1. customdescribed for the preparation of Example 18

Sources & evidence

ORD record
ord-2239f21be2864a2aa3b0b53828b0865a
Source dataset
uspto-grants-2015_07
Patent number
US09073881B2

Reaction notes

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