2-Bromoacetamidopyridine → 2-(3-Bromo-5-iodophenyl)-4-(pyridin-2-yl)-1,3-oxazole

HRID 431993

Reaction equation

HRID 431993 reaction equation
Br[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][N:6]=1)=O.[Br:11][C:12]1[CH:13]=[C:14]([CH:18]=[C:19]([I:21])[CH:20]=1)[C:15]([NH2:17])=[O:16]>C1(C)C=CC=CC=1>[Br:11][C:12]1[CH:13]=[C:14]([C:15]2[O:16][CH:2]=[C:3]([C:5]3[CH:10]=[CH:9][CH:8]=[CH:7][N:6]=3)[N:17]=2)[CH:18]=[C:19]([I:21])[CH:20]=1

Participants

4

Reactant 2

HCID 383842-BromoacetamidopyridineHCID 219424113-Bromo-5-iodobenzamide

Product 1

HCID 102243582-(3-Bromo-5-iodophenyl)-4-(pyridin-2-yl)-1,3-oxazoleYield 1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 2-bromoacetylpyridine (1.0 g, 5 mmol) in toluene (5 mL) was treated with 3-bromo-5-iodobenzamide (2.0 g, 6 mmol) and the mixture heated at reflux for 60 hours. The mixture was then cooled and the solvent was removed in vacuo. Silica gel chromatography using a gradient of hexane to ethyl acetate afforded 10 mg (1%) of 2-(3-bromo-5-iodophenyl)-4-(pyridin-2-yl)-1,3-oxazole: 1H-NMR (CDCl3), δ ppm: 8.62 (d, 1H), 8.42 (m, 1H), 8.38 (s, 1H), 8.24 (m, 1H), 8.00 (t, 1H), 7.95 (d, 1H), 7.8 (m, 1H), 7.27 (m, 1H).

Workup

  1. temperaturethe mixture heated
  2. temperatureat reflux for 60 hours
  3. temperatureThe mixture was then cooled
  4. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-5cc91f94349d446bb16806a7edaf152b
Source dataset
uspto-grants-2003_12
Patent number
US06660753B2

Linked notes

Loading…