2-Bromo-1-(thiophen-2-yl)ethan-1-one → HCID 71536346, compound

HRID 1519301Notes

Reaction equation

HRID 1519301 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[S:28][CH:29]=[CH:30][CH:31]=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[S:28][CH:29]=[CH:30][CH:31]=3)[N:12]=2)=[CH:8][CH:7]=1)([O-:22])=[O:21]

Participants

3

Reactant 2

HCID 27763722-Bromo-1-(thiophen-2-yl)ethan-1-oneHCID 866798322'-Nitro-4-thiocarbamoyl-biphenyl-2-carboxylic acid methyl ester2×

Product 1

HCID 71536346HCID 71536346, compoundYield 47%

Procedure

2′-Nitro-4-(4-thiophen-2-yl-thiazol-2-yl)-biphenyl-2-carboxylic acid (120 mg, 47%) was prepared from 2′-nitro-4-thiocarbamoyl-biphenyl-2-carboxylic acid methyl ester (which may be prepared as described for Intermediate 4) and 2-(2-bromoacetyl)thiophene (available from Maybridge) using the procedure described for the preparation of Example 1. 1H NMR (300 MHz, DMSO-d6) δ 8.51 (d, J=1.7 Hz, 1H), 8.10-8.20 (m, 3H), 7.71 (t, J=8.1 Hz, 1H), 7.57-7.67 (m, 3H), 7.41 (t, J=8.3 Hz, 2H), 7.15 (t, J=4.6 Hz, 2H).

Workup

  1. customdescribed for the preparation of Example 1

Sources & evidence

ORD record
ord-8a297e1f246a49d89309240b27185554
Source dataset
uspto-grants-2015_07
Patent number
US09073881B2

Reaction notes

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