2-Bromo-1-(thiophen-3-yl)ethan-1-one → HCID 71536082, compound

HRID 1519299Notes

Reaction equation

HRID 1519299 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:31]=[CH:30][S:29][CH:28]=1)=O>>[N+:20]([C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=1[C:6]1[C:5]([C:3]([OH:2])=[O:4])=[CH:10][C:9]([C:11]2[S:13][CH:24]=[C:25]([C:27]3[CH:31]=[CH:30][S:29][CH:28]=3)[N:12]=2)=[CH:8][CH:7]=1)([O-:22])=[O:21]

Participants

3

Reactant 2

HCID 27763792-Bromo-1-(thiophen-3-yl)ethan-1-oneHCID 866798322'-Nitro-4-thiocarbamoyl-biphenyl-2-carboxylic acid methyl ester2×

Product 1

HCID 71536082HCID 71536082, compoundYield 19%

Procedure

2′-Nitro-4-(4-thiophen-3-yl-thiazol-2-yl)-biphenyl-2-carboxylic acid (50 mg, 19%) 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-1-(3-thienyl)-1-ethanone (available from Maybridge) using the procedure described for the preparation of Example 1. 1H NMR (300 MHz, DMSO-d6) δ 13.13 (s, 1H), 8.54 (d, J=1.7 Hz, 1H), 8.23 (dd, J=7.8, 1.8 Hz, 1H), 8.04-8.15 (m, 3H), 7.78 (t, J=6.8 Hz, 1H), 7.62-7.69 (m, 3H), 7.44 (t, J=8.1 Hz, 2H).

Workup

  1. customdescribed for the preparation of Example 1

Sources & evidence

ORD record
ord-2d3f15c74c884867adf6828f3b9e99ce
Source dataset
uspto-grants-2015_07
Patent number
US09073881B2

Reaction notes

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