تفاعل #157811

ord-1ddef37346744936946e7026649bb908

ظروف التفاعل

درجة الحرارة
90°CELSIUS
الظروف التفصيلية
See reaction.notes.procedure_details.

المعالجة

  1. 1
    ترشيحthe insoluble matter was filtered off through celite
  2. 2
    استخلاصfollowed by extraction with ethyl acetate
  3. 3
    تجفيفThe organic layer was dried over anhydrous magnesium sulfate
  4. 4
    ترشيحfiltered
  5. 5
    تركيزThe filtrate was concentrated under reduced pressure
  6. 6
    أخرىThe resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=50:50→0:100)

الإجراء التجريبي

1,4-Dioxane (4 mL) and water (0.4 mL) were added to a mixture of (5R)-5-[(Z)-2-bromo-2-(5-cyclopropyl-6-methoxypyridin-2-yl)ethenyl]pyrrolidin-2-one obtained in Reference Example 4-24 (170 mg), 4-chlorophenylboronic acid (160 mg), tris(dibenzylideneacetone) dipalladium (45 mg), tri(2-furyl)phosphine (69 mg) and cesium carbonate (492 mg), and the mixture was stirred at 90° C. for 2.5 hours. Water and ethyl acetate were added to the reaction solution and the insoluble matter was filtered off through celite, followed by extraction with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=50:50→0:100) to give (5R)-5-[(E)-2-(4-chlorophenyl)-2-(5-cyclopropyl-6-methoxypyridin-2-yl)ethenyl]pyrrolidin-2-one as a crude product (250 mg).

المصدر

DOI: 10.6084/m9.figshare.5104873.v1براءة الاختراع: US08822503B2uspto-grants-2014_09