Water → HCID 57928722, compound

Participants

Reaction Steps

To a suspension of methyl (2-{[4-chloro-6-(methylamino)-5-vinylpyridine-3-yl]carbonyl}hydrazino)(oxo)acetate (450 mg) in tetrahydrofuran (7 ml) and dioxane (7 ml) was added diphosphorus pentasulfide (383 mg) under cooling in an ice bath. After the mixture was stirred at ambient temperature for 5 hours. To the reaction mixture was added tetrahydrofuran (10 ml) and diphosphorus pentasulfide (190 mg). After the mixture was stirred at ambient temperature for 2 hours, water was added to the reaction solution, and the pH was adjusted to approximately 10 with aqueous sodium hydroxide, and the solution was extracted with ethyl acetate. The organic layer was dried over magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure. The residue was purified by silica gel chromatography (chloroform:methanol) to obtain methyl-5-(4-chloro-1H-pyrrolo[2,3,b]pyridine-5-yl)-1,3,4-thiadiazole-2-carboxylate (90 mg).

Provenance & Evidence