تفاعل #1983177

ord-a048f82404cc49949b0f2bfa2399be70

معادلة التفاعل

O
water
Cc1cccc(C#CC=C2CCNCC2)n1
Compound
Cc1cccc(C#CC=C2CCNCC2)n1
2-Methyl-6-(3-piperidin-4-ylideneprop-1-ynyl)pyridine
O=[N+]([O-])c1ccc(Br)o1
2-bromo-5-nitrofuran
O=C([O-])[O-].[K+].[K+]
potassium carbonate
Cc1cccc(C#CC=C2CCN(c3ccc([N+](=O)[O-])o3)CC2)n1
2-Methyl-6-{3-[1-(5-nitrofuran-2-yl)piperidin-4-ylidene]prop-1-yn-1-yl}pyridine

المذيبات

ظروف التفاعل

الظروف التفصيلية
See reaction.notes.procedure_details.

المعالجة

  1. 1
    استخلاصextracted with EtOAc
  2. 2
    غسيلThe combined organic layers were washed with brine
  3. 3
    أخرىdried on Na2SO4
  4. 4
    أخرىevaporated to dryness in vacuo
  5. 5
    أخرىto afford a residue, which
  6. 6
    أخرىwas purified by flash chromatography
  7. 7
    غسيلeluting with Petroleum Ether-EtOAc 6:4 affording the title product (94 mg) as a yellow solid

الإجراء التجريبي

A suspension of the Compound of Example 3 (100 mg, 0.47 mmol), 2-bromo-5-nitrofuran (98 mg, 0.51 mmol) and potassium carbonate (72 mg, 0.52 mmol) in DMF (2 mL) was stirred at r.t. for 4 h. Afterwards, the reaction mixture was poured into water and extracted with EtOAc. The combined organic layers were washed with brine, dried on Na2SO4 and evaporated to dryness in vacuo to afford a residue, which was purified by flash chromatography eluting with Petroleum Ether-EtOAc 6:4 affording the title product (94 mg) as a yellow solid.

المصدر

DOI: 10.6084/m9.figshare.5104873.v1براءة الاختراع: US08518916B2uspto-grants-2013_08