Butyl isocyanate → HCID 54043146, compound

Participants

Reaction Steps

To a stirred solution consisting of 3-methyl-1-(propyl-4-pyridinylamino)-1H-indol-5-ol (2.11 g) and tetrahydrofuran (50 ml) was added milled K2CO3 (1.09 g), followed by dropwise addition of butyl isocyanate (0.93 ml) at room temperature under nitrogen. Stirring was continued for 2.0 hours at which time the reaction mixture was filtered through a pad of celite and the solids washed with EtOAc. Concentration afforded the crude product. Purification via flash column chromatography (silica gel, 2% Et3N/EtOAc) afforded 2.65 g of the desired carbamate as an oil. This oil was dissolved in a small amount of EtOAc and diluted with ether, whereupon the product crystallized as a white powder, m.p. 120°-122° C.

Provenance & Evidence