4-Bromophenacyl bromide → HCID 71536903, compound

HRID 1519283Notes

Reaction equation

HRID 1519283 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].Br[CH2:24][C:25]([C:27]1[CH:32]=[CH:31][C:30]([Br:33])=[CH:29][CH:28]=1)=O>>[Br:33][C:30]1[CH:31]=[CH:32][C:27]([C:25]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:24]=2)=[CH:28][CH:29]=1

Participants

3

Reactant 2

HCID 74544-Bromophenacyl bromideHCID 866798322'-Nitro-4-thiocarbamoyl-biphenyl-2-carboxylic acid methyl ester2×

Product 1

HCID 71536903HCID 71536903, compoundYield 68%

Procedure

4-[4-(4-Bromo-phenyl)-thiazol-2-yl]-2′-nitro-biphenyl-2-carboxylic acid (205 mg, 68%) was prepared from 2′-nitro-4-thiocarbamoyl-biphenyl-2-carboxylic acid methyl ester (which may be prepared as described for Intermediate 4) and 2,4′-dibromoacetophenone (available from Alfa Aesar) 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), 8.34 (s, J=8.3, 1H), 8.25 (dd, J=8.0, 2.0 Hz, 1H), 8.14 (dd, J=8.1, 1.1 Hz, 1H), 8.03 (d, J=8.6 Hz, 1H), 7.62-7.81 (m, 4H), 7.40-7.47 (m, 2H).

Workup

  1. customdescribed for the preparation of Example 1

Sources & evidence

ORD record
ord-6976fe2dee9642b58a3ef833b2615bec
Source dataset
uspto-grants-2015_07
Patent number
US09073881B2

Reaction notes

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