تفاعل #92359

ord-58880dbf79124678b073a50a8366605f

معادلة التفاعل

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
المردود 89.5%

الكواشف

لا شيء

المذيبات

ظروف التفاعل

الظروف التفصيلية
See reaction.notes.procedure_details.

المعالجة

  1. 1
    أخرىThe mixture was quenched
  2. 2
    استخلاصextracted as in Intermediate Example 5(a)
  3. 3
    workup.DISTILLATIONThe solvent was distilled off
  4. 4
    أخرىto give the product in 89.5% yield
  5. 5
    أخرى263 [M+H]+ (rt: 1.57 min)

الإجراء التجريبي

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).

المصدر

DOI: 10.6084/m9.figshare.5104873.v1براءة الاختراع: US09447091B2uspto-grants-2016_09