2-Bromo-2',4'-difluoroacetophenone → HCID 71537196, compound

HRID 1519275Notes

Reaction equation

HRID 1519275 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]([F:33])=[CH:29][C:28]=1[F:34])=O>>[F:34][C:28]1[CH:29]=[C:30]([F:33])[CH:31]=[CH:32][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

3

Reactant 2

HCID 27741852-Bromo-2',4'-difluoroacetophenoneHCID 866798322'-Nitro-4-thiocarbamoyl-biphenyl-2-carboxylic acid methyl ester2×

Product 1

HCID 71537196HCID 71537196, compoundYield 23%

Procedure

4-[4-(2,4-Difluoro-phenyl)-thiazol-2-yl]-2′-nitro-biphenyl-2-carboxylic acid (66 mg, 23%) 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′,4′-difluoroacetophenone (available from Matrix Scientific) using the procedure described for the preparation of Example 18. 1H NMR (300 MHz, DMSO-d6) δ 8.57 (d, J=1.4 Hz, 2H), 8.10-8.35 (m, 4H), 7.21-7.33 (m, 3H), 7.77 (t, J=7.5 Hz, 1H), 7.64 (t, J=7.7 Hz, 1H), 7.23-7.50 (m, 4H).

Workup

  1. customdescribed for the preparation of Example 18

Sources & evidence

ORD record
ord-2603321224f84cb599bc51c27f364f60
Source dataset
uspto-grants-2015_07
Patent number
US09073881B2

Reaction notes

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