2-Bromo-1-(5-bromothiophen-2-yl)ethan-1-one → HCID 71536631, compound

HRID 1519281Notes

Reaction equation

HRID 1519281 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[S:28][C:29]([Br:32])=[CH:30][CH:31]=1)=O>>[Br:32][C:29]1[S:28][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:31][CH:30]=1

Participants

3

Reactant 2

HCID 19883982-Bromo-1-(5-bromothiophen-2-yl)ethan-1-oneHCID 866798322'-Nitro-4-thiocarbamoyl-biphenyl-2-carboxylic acid methyl ester2×

Product 1

HCID 71536631HCID 71536631, compoundYield 33%

Procedure

4-[4-(5-Bromo-thiophen-2-yl)-thiazol-2-yl]-2′-nitro-biphenyl-2-carboxylic acid (180 mg, 33%) was prepared from 2′-nitro-4-thiocarbamoyl-biphenyl-2-carboxylic acid methyl ester (which may be prepared as described for Intermediate 4) and 2-bromo-1-(5-bromothiophen-2-yl)ethanone (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), 8.50 (d, J=1.8 Hz, 1H), 8.13-8.22 (m, 3H), 7.52 (d, J=3.9 Hz, 1H), 7.40-7.48 (m, 2H), 7.28 (d, J=3.9 Hz, 1H).

Workup

  1. customdescribed for the preparation of Example 1

Sources & evidence

ORD record
ord-986348c0c53a4cb4a5c4314be947742f
Source dataset
uspto-grants-2015_07
Patent number
US09073881B2

Reaction notes

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