反应 #2487463

ord-a549ce7812664e109cd1827f3f9aba9e

反应方程式

O
Water
O=C([O-])O.[Na+]
sodium hydrogen carbonate
Cl.NO
hydroxylamine hydrochloride
COc1ccc2c(c1)cc(-c1ccccc1)n2Cc1cccc(C#N)n1
6-(5-methoxy-2-phenylindol-1-ylmethyl)pyridine-2-carbonitrile
COc1ccc2c(c1)cc(-c1ccccc1)n2Cc1cccc(C(N)=NO)n1
title compound
收率 99.1%
COc1ccc2c(c1)cc(-c1ccccc1)n2Cc1cccc(C(N)=NO)n1
6-(5-Methoxy-2-phenylindol-1-ylmethyl)pyridine-2-carboxamidoxime
收率 99.1%

反应条件

温度
50°CELSIUS
详细条件
See reaction.notes.procedure_details.

后处理

  1. 1
    workup.STIRRINGby stirring at 80° C. overnight
  2. 2
    萃取followed by extraction with ethyl acetate
  3. 3
    洗涤The organic layer was washed with water and saturated brine
  4. 4
    干燥dried over anhydrous magnesium sulfate
  5. 5
    浓缩concentrated under reduced pressure

实验过程

To a suspension of hydroxylamine hydrochloride (233 mg) in dimethylsulfoxide (1.7 mL) was added sodium hydrogen carbonate (338 mg), and this mixture was stirred at 50° C. for 1 hour. Subsequently, 6-(5-methoxy-2-phenylindol-1-ylmethyl)pyridine-2-carbonitrile (114 mg) was added thereto, followed by stirring at 80° C. overnight. Water was added to the reaction mixture, followed by extraction with ethyl acetate. The organic layer was washed with water and saturated brine, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure to obtain the title compound (124 mg). 1H-NMR (DMSO-d6) δ ppm: 3.76 (3H, s), 5.51 (2H, s), 5.65 (2H, br s), 6.59 (1H, s), 6.70-6.85 (2H, m), 7.11 (1H, d, J=2.4 Hz), 7.32 (1H, d, J=8.9 Hz), 7.35-7.70 (7H, m), 9.92 (1H, s).

来源

DOI: 10.6084/m9.figshare.5104873.v1专利: US08796247B2uspto-grants-2014_08