Reacción #92359

ord-58880dbf79124678b073a50a8366605f

Ecuación de reacción

Ic1cn[nH]c1
4-iodo-1H-pyrazole
O=C([O-])[O-].[K+].[K+]
K2CO3
BrC1CCCC1
bromocyclopentane
Ic1cnn(C2CCCC2)c1
1-Cyclopentyl-4-iodo-1H-pyrazole
Rendimiento 89.5%

Disolventes

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    OtroThe mixture was quenched
  2. 2
    Extracciónextracted as in Intermediate Example 5(a)
  3. 3
    workup.DISTILLATIONThe solvent was distilled off
  4. 4
    Otroto give the product in 89.5% yield
  5. 5
    Otro263 [M+H]+ (rt: 1.57 min)

Procedimiento

To a solution of 4-iodo-1H-pyrazole (5 g, 25.78 mmol, 1.0 eq.) in DMF (25 ml) were added K2CO3 (8.908 g, 64.45 mmol, 2.5 eq.) and bromocyclopentane (4.96 g, 33.51 mmol, 1.3 eq.). The mixture was stirred at RT for 12 h. The mixture was quenched and extracted as in Intermediate Example 5(a). The solvent was distilled off to give the product in 89.5% yield. 1H NMR (300 MHz, CDCl3): δ 7.49 (s, 1H), 7.45 (s, 1H), 4.66-4.62 (m, 1H), 2.17-2.02 (m, 1H), 2.00-1.96 (m, 2H), 1.93-1.78 (m, 2H), 1.73-1.67 (m, 2H). LC-MS (ESI): Calculated mass: 262; Observed mass: 263 [M+H]+ (rt: 1.57 min).

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US09447091B2uspto-grants-2016_09