合成路线1

The reaction of 6-(trifluoromethyl)indoline (I) with potassium thiocyanate and Br2 in methanol gives 5-thiocyanato-6-(trifluoromethyl)indoline (II), which is treated with ammonia in hot dioxane/water yielding the disulfide (III). The acylation of (III) with acetic anhydride and triethylamine in dichloromethane affords the corresponding diacetyl derivative (IV), which is treated with triphenylphosphine and conc. HCl in refluxing dioxane to give 5-sulfanyl-6-(trifluoromethyl)-indoline (V). The methylation of (V) with methyl iodide and K2CO3 in hot DMF yields the methylsulfanyl compound (VI), which is deacetylated with NaOH in refluxing ethanol/water affording 5-(methylmsulfanyl)-6--(trifluoromethyl)-indoline (VII). Finally, this compound is condensed with 3-pyridyl isothiocyanate (VIII) in toluene. The indoline (VII) can also be obtained directly from indoline (I) by reaction of (I) with potassium thiocyanate and Br2 in methanol, followed by a treatment with methyl iodide and KOH. The 3-pyridyl isocyanate can be obtained by decomposition of pyridine-3-carboxylic acid azide (IX) in refluxing toluene.