2-Bromo-4'-(methylsulfonyl)acetophenone → HCID 71536906, compound

HRID 1519290Notes

Reaction equation

HRID 1519290 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]([S:33]([CH3:36])(=[O:35])=[O:34])=[CH:29][CH:28]=1)=O>>[CH3:36][S: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)(=[O:34])=[O:35]

Participants

3

Reactant 2

HCID 7358232-Bromo-4'-(methylsulfonyl)acetophenoneHCID 866798322'-Nitro-4-thiocarbamoyl-biphenyl-2-carboxylic acid methyl ester2×

Product 1

HCID 71536906HCID 71536906, compoundYield 11%

Procedure

4-[4-(4-Methanesulfonyl-phenyl)-thiazol-2-yl]-2′-nitro-biphenyl-2-carboxylic acid (33 mg, 11%) 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-[4-(methylsulfonyl)phenyl]-1-ethanone (available from TCI America) using the procedure described for the preparation of Example 1. 1H NMR (300 MHz, DMSO-d6) δ 8.57 (d, J=8.3 Hz, 2H), 8.27-8.35 (m, 3H), 8.14 (d, J=7.8 Hz, 1H), 8.03 (d, J=8.1 Hz, 1H), 7.79 (t, J=8.4 Hz, 1H), 7.65 (t, J=7.6 Hz, 1H), 7.41-7.48 (m, 2H), 3.26 (s, 3H).

Workup

  1. customdescribed for the preparation of Example 1

Sources & evidence

ORD record
ord-bc3e26e28a46453b96bd08e226212f06
Source dataset
uspto-grants-2015_07
Patent number
US09073881B2

Reaction notes

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