3-(2-Bromoacetyl)benzonitrile → HCID 71537192, compound

HRID 1519292Notes

Reaction equation

HRID 1519292 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:28]=[C:29]([CH:32]=[CH:33][CH:34]=1)[C:30]#[N:31])=O>>[C:30]([C:29]1[CH: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:34]=[CH:33][CH:32]=1)#[N:31]

Participants

3

Reactant 2

HCID 27358673-(2-Bromoacetyl)benzonitrileHCID 866798322'-Nitro-4-thiocarbamoyl-biphenyl-2-carboxylic acid methyl ester2×

Product 1

HCID 71537192HCID 71537192, compoundYield 56%

Procedure

4-[4-(3-Cyano-phenyl)-thiazol-2-yl]-2′-nitro-biphenyl-2-carboxylic acid (150 mg, 56%) was prepared from 2′-nitro-4-thiocarbamoyl-biphenyl-2-carboxylic acid methyl ester (which may be prepared as described for Intermediate 4) and 3-(2-bromoacetyl)benzonitrile (available from Oakwood Products, Inc.) using the procedure described for the preparation of Example 1. 1H NMR (300 MHz, DMSO-d6) δ 13.17 (s, 1H), 8.59 (d, J=1.6 Hz, 1H), 8.54 (s, 1H), 8.51 (s, 1H), 8.44 (d, J=7.7 Hz, 1H), 8.31 (dd, J=8.0, 1.6 Hz, 1H), 8.16 (d, J=7.5 Hz, 1H), 7.64-7.88 (m, 4H), 7.43-7.49 (m, 2H).

Workup

  1. customdescribed for the preparation of Example 1

Sources & evidence

ORD record
ord-158ce9a1f5c74dc0b989740bf76d6952
Source dataset
uspto-grants-2015_07
Patent number
US09073881B2

Reaction notes

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