Reacción #2006429

ord-f49cf50d9c584db7a357f1696e0bb689

Ecuación de reacción

O
H2O
Cc1cccc(-c2ncc[nH]2)n1
2-(6-Methyl-2-pyridyl)imidazole
CC(C)(C)[O-].[Na+]
sodium t-butoxide
O=C1c2ccccc2C(=O)N1CCCCCCBr
N-(6-bromohexyl)phthalimide
Cc1cccc(-c2nccn2CCCCCCN2C(=O)c3ccccc3C2=O)n1
2-(6-methyl-2-pyridyl)-1-(6-(phthalimido)hexyl)imidazole

Disolventes

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    workup.WAITat 60° C. for 3.5 h
  2. 2
    Extracciónextracted three times with EtOAc (3×100 mL)
  3. 3
    ExtracciónThe combined EtOAc extract
  4. 4
    Secadowas dried with anhydrous Na2SO4
  5. 5
    Otroevaporated to dryness
  6. 6
    OtroThe product was purified by a silica gel column

Procedimiento

To a solution of 2-(6-Methyl-2-pyridyl)imidazole (2.16 g) and sodium t-butoxide (1.57 g) in 50 mL dry DMF was added N-(6-bromohexyl)phthalimide (4.72 g). The resulting solution was stirred at room temperature for 3 h and then at 60° C. for 3.5 h. The solution was poured into H2O (80 mL) and then extracted three times with EtOAc (3×100 mL). The combined EtOAc extract was dried with anhydrous Na2SO4, and then evaporated to dryness. The product was purified by a silica gel column using EtOAc as the eluent. Yield: about 4.2 g.

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US08168052B2uspto-grants-2012_05