Cesium carbonate → HCID 89560502, compound

Participants

Reaction Steps

DMCDA (85 μL, 0.538 mmol) followed by 1H-1,2,3-triazole (0.31 mL, 5.38 mmol) were added to a mixture of rac-5-(3-iodo-benzyl)-5-methyl-morpholin-3-one H-8 (890 mg, 2.69 mmol), Cs2CO3 (1.75 g, 5.38 mmol) and CuI (77 mg, 0.40 mmol) in DMF (5 mL) under argon and the resulting blue suspension was heated to 120° C. for 18 h. The reaction mixture was cooled to RT before being quenched with water and filtered over celite rinsing with water and DCM. The layers were separated and the aqueous phase was re-extracted with DCM (2×). The combined organic extracts were washed with brine, dried over Na2SO4, filtered and evaporated in vacuo. The crude product was purified by flash chromatography (eluting with a gradient of 75% to 100% EtOAc in hexane) to give the title compound as a pale brown solid. LC-MS A: tR=0.69 min; [M+H]+=273.21.

Provenance & Evidence