Phenylacetylene → HCID 19851598, compound

Participants

Reaction Steps

5.1 g of 5,6-dihydro-7-iodo-5-methyl-4H-imidazo[1,5-a]thieno[3,2-f][1,4]diazepine-one (prepared in accordance with Example 73) was dissolved in 47 ml of diethylamine and 20 ml of dimethylformamide. 1.75 ml of phenylacetylene, 105 mg of bis-(triphenylphosphine)-palladium(II) chloride and 17 mg of copper(I) iodide were then added. The mixture was stirred at room temperature for 2 hours and then concentrated in a vacuum. The residue was diluted with 200 ml of dichloromethane and washed twice with water. The aqueous washings were extracted twice with dichloromethane. The combined dichloromethane solutions were dried over sodium sulphate and chromatographed through 300 g of silica gel. Elution was carried out first with trichloromethane and trichloromethane/ethanol mixtures 199:1 and 99:1. There was then eluted with a trichloromethane/ethanol mixture 97:3 an oily substance which can be crystallized from isopropanol/water. After repeated recrystallizations from isopropanol/water there was obtained 5,6-dihydro-5-methyl-7-(phenylethynyl)-4H-imidazo[1,5-a]thieno[3,2-f][1,4]diazepine one of melting point 143°-144°.

Provenance & Evidence