2-Fluoro-4-methoxyphenacyl bromide → HCID 71536902, compound

HRID 1519285Notes

Reaction equation

HRID 1519285 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].[F:23][C:24]1[CH:33]=[C:32]([O:34][CH3:35])[CH:31]=[CH:30][C:25]=1[C:26](=O)[CH2:27]Br>>[F:23][C:24]1[CH:33]=[C:32]([O:34][CH3:35])[CH:31]=[CH:30][C:25]=1[C:26]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:27]=1

Participants

3

Reactant 2

HCID 51195912-Fluoro-4-methoxyphenacyl bromideHCID 866798322'-Nitro-4-thiocarbamoyl-biphenyl-2-carboxylic acid methyl ester2×

Product 1

HCID 71536902HCID 71536902, compoundYield 89%

Procedure

4-[4-(2-Fluoro-4-methoxy-phenyl)-thiazol-2-yl]-2′-nitro-biphenyl-2-carboxylic acid (253 mg, 89%) was prepared from 2′-nitro-4-thiocarbamoyl-biphenyl-2-carboxylic acid methyl ester (which may be prepared as described for Intermediate 4) and 2-fluoro-4-methoxyphenacyl bromide (available from ASDI Incorporated) using the procedure described for the preparation of Example 1. 1H NMR (300 MHz, DMSO-d6) δ 8.54 (d, J=1.8 Hz, 1H), 8.10-8.21 (m, 3H), 7.94 (d, J=2.4 Hz, 1H), 7.59-7.78 (m, 2H), 7.39 (d, J=8.0 Hz, 2H), 6.93-7.02 (m, 2H), 3.83 (s, 3H).

Workup

  1. customdescribed for the preparation of Example 1

Sources & evidence

ORD record
ord-41fbac293737420fbb97ce15ad3bdbe3
Source dataset
uspto-grants-2015_07
Patent number
US09073881B2

Reaction notes

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