Bromomethyl 3-methoxyphenyl ketone → HCID 71536905, compound

HRID 1519287Notes

Reaction equation

HRID 1519287 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].[CH3:23][O:24][C:25]1[CH:30]=[C:29]([C:31]([CH2:33]Br)=O)[CH:28]=[CH:27][CH:26]=1>>[CH3:23][O:24][C:25]1[CH:30]=[C:29]([C:31]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:33]=2)[CH:28]=[CH:27][CH:26]=1

Participants

3

Reactant 2

HCID 101294Bromomethyl 3-methoxyphenyl ketoneHCID 866798322'-Nitro-4-thiocarbamoyl-biphenyl-2-carboxylic acid methyl ester2×

Product 1

HCID 71536905HCID 71536905, compoundYield 54%

Procedure

4-[4-(3-Methoxy-phenyl)-thiazol-2-yl]-2′-nitro-biphenyl-2-carboxylic acid (148 mg, 54%) was prepared from 2′-nitro-4-thiocarbamoyl-biphenyl-2-carboxylic acid methyl ester (which may be prepared as described for Intermediate 4) and 3′-methoxyphenacyl bromide (available from Aldrich Chemical Company, Inc.) using the procedure described for the preparation of Example 1. 1H NMR (300 MHz, DMSO-d6) δ 8.56 (d, J=1.9 Hz, 1H), 8.30 (s, 1H), 8.27 (dd, J=6.0, 2.0 Hz, 1H), 8.15 (dd, J=8.1, 1.1 Hz, 1H), 7.76-7.82 (m, 1H), 7.61-7.69 (m, 3H), 7.38-7.48 (m, 3H), 6.97 (dd, J=8.2, 2.4 Hz, 1H).

Workup

  1. customdescribed for the preparation of Example 1

Sources & evidence

ORD record
ord-46fc37eaebd1438b80b5584cdf253423
Source dataset
uspto-grants-2015_07
Patent number
US09073881B2

Reaction notes

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