Propargyl alcohol → HCID 86654732, compound

Participants

Reaction Conditions

Reaction Steps

To an oven dried glass pressure vessel was added tert-butyl (1S,2R)-2-(7-iodo-3-oxo-4-(m-tolylamino)-2,3-dihydro-1H-pyrrolo[3,4-c]pyridin-6-ylamino)cyclohexylcarbamate (25 mg, 0.043 mmol), copper(I) iodide (12.37 mg, 0.065 mmol), bis(triphenylphosphine) palladium(II)chloride (9.12 mg, 0.013 mmol), butylated hydroxytoluene (one granule), THF (866 μL), and Et3N (121 μL, 0.866 mmol). The mixture was degassed 3 min with nitrogen. Propargyl alcohol (31 μL, 0.520 mmol) was added and the vessel was capped and heated at 80° C. with stirring for 2 h and then at RT for 12 h. The reaction mixture was diluted with EtOAc (10 mL) and washed with water (5 mL) and brine (5 mL). The organic layer was collected, dried with Na2SO4, and concentrated to give the title compound as a brown residue, which was used without further purification (22 mg, 101%). [M+H] calc'd for C28H35N5O4, 506; found, 506.

Provenance & Evidence