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

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A solution of tert-butyl methylcarbamate (35.0 mg, 0.27 mmol) in dioxane (1.781 ml) was added to a stirred mixture of 6-(2-morpholino-4-oxo-4H-chromen-8-yl)dibenzo[b,d]thiophen-2-yl trifluoromethanesulfonate (100 mg, 0.18 mmol), TRIS(DIBENZYLIDENEACETONE)DIPALLADIUM(0) (4.08 mg, 4.45 µmol), (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (5.15 mg, 8.90 µmol) and cesium carbonate (232 mg, 0.71 mmol). The resulting mixture was stirred under nitrogen at 110 °C for 3 hours. The cooled reaction mixture was diluted with methanol and the residue was purified by ion exchange chromatography, using an SCX column. The desired product was eluted from the column using 7M NH3/MeOH and evaporated to dryness to afford tert-butyl methyl(6-(2-morpholino-4-oxo-4H-chromen-8-yl)dibenzo[b,d]thiophen-2-yl)carbamate (97 mg, 100 %) as a orange residue. 100% assumed and this was progressed to the next stage with no further purification.

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