3-(2-Bromoacetyl)pyridine hydrobromide → HCID 71535810, compound

HRID 1519295Notes

Reaction equation

HRID 1519295 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.Br[CH2:25][C:26]([C:28]1[CH:29]=[N:30][CH:31]=[CH:32][CH:33]=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:25]=[C:26]([C:28]3[CH:29]=[N:30][CH:31]=[CH:32][CH:33]=3)[N:12]=2)=[CH:8][CH:7]=1)([O-:22])=[O:21]

Participants

3

Reactant 2

HCID 27762343-(2-Bromoacetyl)pyridine hydrobromideHCID 866798322'-Nitro-4-thiocarbamoyl-biphenyl-2-carboxylic acid methyl ester2×

Product 1

HCID 71535810HCID 71535810, compoundYield 47%

Procedure

2′-Nitro-4-(4-pyridin-3-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 3-(bromoacetyl)pyridine hydrobromide (available from Oakwood Products, Inc.) using the procedure described for the preparation of Example 1. 1H NMR (300 MHz, DMSO-d6) δ 9.32 (d, J=1.9 Hz, 1H), 8.64 (dd, J=4.8, 1.4 Hz, 1H), 8.55-8.58 (m, 2H), 8.50 (s, 1H), 8.29 (dd, J=8.0, 2.0 Hz, 1H), 8.14 (dd, J=8.0, 1.2 Hz, 1H), 7.76-7.81 (m, 1H), 7.62-7.68 (m, 2H), 7.41-7.49 (m, 1H).

Workup

  1. customdescribed for the preparation of Example 1

Sources & evidence

ORD record
ord-ae23f2c5d3a0427783089f5c9d03160c
Source dataset
uspto-grants-2015_07
Patent number
US09073881B2

Reaction notes

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