تفاعل #1668901

معادلة التفاعل

2-[2-(5-Nitro-1H-indol-3-yl)-ethyl]-isoindole-1,3-dione

phenylboronic acid

sodium carbonate

lithium chloride

→

2-[2-(5-nitro-2-phenyl-1H-indol-3-yl)-ethyl]-isoindole-1,3-dione

المذيبات

THF chloroform

ظروف التفاعل

المعالجة

1. 1
   غسيلeluted from a silica column with chloroform-methanol
2. 2
   workup.DISSOLUTIONThe product is dissolved in toluene-ethanol (1:1)
3. 3
   درجة الحرارةThe mixture is refluxed 4 h
4. 4
   تركيزconcentrated in vacuo
5. 5
   أخرىthe oil chromatographed on silica
6. 6
   غسيلeluted with ethyl acetate-hexane

الإجراء التجريبي

2-[2-(5-Nitro-1H-indol-3-yl)-ethyl]-isoindole-1,3-dione (1 mmol) is dissolved in THF/chloroform (1:1) and treated with pyridine hydrobromide perbromide at 0° C. for 90 min, then eluted from a silica column with chloroform-methanol. The product is dissolved in toluene-ethanol (1:1) and treated with phenylboronic acid (1.5 equiv), sodium carbonate (2.5 equiv), lithium chloride (3 equiv), and palladium tetrakis(triphenylphosphine) (5 mol %). The mixture is refluxed 4 h, concentrated in vacuo, and the oil chromatographed on silica eluted with ethyl acetate-hexane to afford 2-[2-(5-nitro-2-phenyl-1H-indol-3-yl)-ethyl]-isoindole-1,3-dione. This compound is dissolved in ethanol (6 mL) and refluxed with ethylenediamine (3 equiv) 18 h. The solvent is removed in vacuo and the material acetylated with pyridine-acetic anhydride (1:1, 6 mL). The solvent is removed in vacuo and the residue chromatographed on silica eluted with ethyl acetate-hexane. This product is hydrogenated and transformed to the carbamic acid methyl ester as in the example above. Purified product is isolated by reverse-phase HPLC.

المصدر