Acetamide → HCID 58179509, compound

HRID 253960Notes

Reaction equation

HRID 253960 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:9](=O)[CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([Cl:17])[C:12]=2[Cl:18])[C:5]([Cl:8])=[N:6][CH:7]=1.OI(C1C=CC=CC=1)OS(C1C=CC([N+]([O-])=O)=CC=1[N+]([O-])=O)(=O)=O.[C:44]([NH2:47])(=[O:46])[CH3:45]>C1COCC1.ClCCCl.CO>[Br:1][C:2]1[CH:3]=[C:4]([C:9]2[N:47]=[C:44]([CH3:45])[O:46][C:10]=2[C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([Cl:17])[C:12]=2[Cl:18])[C:5]([Cl:8])=[N:6][CH:7]=1

Participants

7

Reactant 3

HCID 178AcetamideHCID 11236711HCID 11236711, compoundHCID 58179505HCID 58179505, compound

Product 1

HCID 58179509HCID 58179509, compoundYield 24%

Reagents, catalysts & solvents 3

HCID 111,2-DichloroethaneSolventHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1-(5-bromo-2-chloropyridin-3-yl)-2-(2,3-dichlorophenyl)ethanone (0.315 g, 0.83 mmol) in THF (3 mL) was added HDNIB (0.585 g, 1.2 mmol, [hydroxy(2,4-dinitrobenzenesulfonyloxy)iodo]benzene, see Lee et al., Synlett, 10: 1563-1564, 2001) in 1,2-dichloroethane (3 mL). The reaction mixture was heated to reflux in a sealed tube for 2 hours, at which point a solution formed. The reaction was cooled to RT and acetamide (2 eq., 0.115 g, 1.9 mmol) was added. The reaction was then heated to reflux for 18 hours. After cooling, the mixture was dissolved in MeOH, adsorbed onto Celite™ and purified by silica gel chromatography (5 to 40% EtOAc/hexanes) to give 5-bromo-2-chloro-3-(5-(2,3-dichlorophenyl)-2-methyloxazol-4-yl)pyridine as a colorless oil [0.084 g, 24% yield; LC-MS m/e=418.8 (M+H)].

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux in a sealed tube for 2 hours, at which point a solution
  3. customformed
  4. temperatureThe reaction was then heated
  5. temperatureto reflux for 18 hours
  6. temperatureAfter cooling
  7. custompurified by silica gel chromatography (5 to 40% EtOAc/hexanes)

Sources & evidence

ORD record
ord-dd13826e14164f429ec4db71e988329e
Source dataset
uspto-grants-2011_01
Patent number
US07872031B2

Reaction notes

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