2-Bromoacetamidopyridine → 2-(3-Chlorophenyl)-4-(pyridin-2-yl)-1,3-oxazole

HRID 2216794Notes

Reaction equation

HRID 2216794 reaction equation
Br[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][N:6]=1)=O.[Cl:11][C:12]1[CH:13]=[C:14]([CH:18]=[CH:19][CH:20]=1)[C:15]([NH2:17])=[O:16]>C1(C)C=CC=CC=1>[Cl: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]=[CH:19][CH:20]=1

Participants

4

Reactant 2

HCID 383842-BromoacetamidopyridineHCID 692543-Chlorobenzamide

Product 1

HCID 102207452-(3-Chlorophenyl)-4-(pyridin-2-yl)-1,3-oxazoleYield 24.7%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Using the procedures of Kelly et al., J. Org. Chem., (1996) 61:4623–4633, a solution of 2-bromoacetylpyridine (120 mg, 0.6 mmol) in toluene (5 mL) was treated with 3-chlorobenzamide (300 mg, 1.9 mmol) and the mixture heated in a sealed vial 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 38 mg (9%) of 2-[3-chlorophenyl]-4-[pyridin-2-yl]-1,3-oxazole as a pale yellow solid. 1H-NMR (CDCl3), δ (ppm): 8.62 (d, 1H), 8.35 (s, 1H), 8.15 (m, 1H), 8.00 (m, 2H), 7.80 (td, 1H), 7.42 (m, 2H), 7.23 (m, 1H).

Workup

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

Sources & evidence

ORD record
ord-82f2d1b0e4f8484e8fe0bf8cfc4ab7a5
Source dataset
uspto-grants-2006_09
Patent number
US07112595B2

Reaction notes

Loading…