Hexane → HCID 54026803, compound

Participants

Reaction Steps

A stirred slurry of hexane washed potassium hydride (0.423 g, 10.6 mmol) in 50 mL of dry THF was treated portionwise with 5-chloroindole (1.6 g, 10.6 mmol). The mixture was stirred until a clear solution was obtained. A solution of (1,3,5-trimethyl-pyrazol-4-yl)-isothiocyanate (1.8 g, 10.6 mmol) of step A in 5 mL THF was slowly added and stirring was continued for 1 hour. The reaction mixture was concentrated in vacuo and the residue partitioned between EtOAc and 1N HCl. The organic layer was washed with brine, dried over Na2SO4 and concentrated in vacuo. The residual solid foam was triturated with Et2O-hexane overnight to provide 2.0 g of the title compound as a tan solid, m.p. 165-166° C. (59% of theory).

Provenance & Evidence