2,6-Difluorophenacyl bromide → 4-[4-(2,6-Difluoro-phenyl)-thiazol-2-yl]-2'-nitro-biphenyl-2-carboxylic acid

HRID 1519276Notes

Reaction equation

HRID 1519276 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[C:32]([F:33])=[CH:31][CH:30]=[CH:29][C:28]=1[F:34])=O>O>[F:33][C:32]1[CH:31]=[CH:30][CH:29]=[C:28]([F:34])[C:27]=1[C:25]1[N:12]=[C:11]([C:9]2[CH:10]=[C:5]([C:3]([OH:2])=[O:4])[C:6]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=3[N+:20]([O-:22])=[O:21])=[CH:7][CH:8]=2)[S:13][CH:24]=1

Participants

4

Reactant 2

HCID 27782632,6-Difluorophenacyl bromideHCID 866798322'-Nitro-4-thiocarbamoyl-biphenyl-2-carboxylic acid methyl ester2×

Product 1

HCID 715386034-[4-(2,6-Difluoro-phenyl)-thiazol-2-yl]-2'-nitro-biphenyl-2-carboxylic acidYield 16%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

4-[4-(2,6-Difluoro-phenyl)-thiazol-2-yl]-2′-nitro-biphenyl-2-carboxylic acid (45 mg, 16%) 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-2′,6′-difluoroacetophenone (available from SynQuest Laboratories, Inc.) using the procedure described for the preparation of Example 18 except that the entire 4 mL of water was added at the beginning of the hydrolysis step rather than being added in two portions. 1H NMR (300 MHz, DMSO-d6) δ 8.45 (d, J=1.9 Hz, 1H), 7.94-8.04 (m, 3H), 7.50-7.70 (m, 3H), 7.19-7.32 (m, 4H).

Workup

  1. additionwas added at the beginning of the hydrolysis step rather
  2. additionthan being added in two portions

Sources & evidence

ORD record
ord-f36bb8122b114fc794e347d090aedf6f
Source dataset
uspto-grants-2015_07
Patent number
US09073881B2

Reaction notes

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