tert-Butyl methylcarbamate → tert-butyl N-methyl-N-[6-(2-morpholin-4-yl-4-oxochromen-8-yl)dibenzothiophen-2-yl]carbamate

Participants

Reaction Conditions

Reaction Steps

6-(2-morpholino-4-oxo-4H-chromen-8-yl)dibenzo[b,d]thiophen-2-yl trifluoromethanesulfonate (207.4 mg, 0.37 mmol), tert-butyl methylcarbamate (194 mg, 1.48 mmol), (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (10.69 mg, 0.02 mmol) and cesium carbonate (481 mg, 1.48 mmol) were suspended in dioxane (6 mL) and sealed into a microwave tube. The reaction was heated to 140 °C for 1 hour in the microwave reactor and cooled to RT. The reaction mixture was filtered then silica gel (2 g) added. The mixture was concentrated _in vacuo_ to yield a white powder which was purified by flash silica chromatography, elution gradient 0 to 5% MeOH in DCM. Pure fractions were evaporated to dryness to afford tert-butyl methyl(6-(2-morpholino-4-oxo-4H-chromen-8-yl)dibenzo[b,d]thiophen-2-yl)carbamate (70.0 mg, 34.9 %) as a white solid.

Provenance & Evidence