Pyrazole → HCID 118117834, compound

Participants

Reaction Steps

A mixture of (R)-5-(3-iodo-benzyl)-morpholin-3-one A-10 (1.0 g, 3.15 mmol), pyrazole (322 mg, 4.73 mmol), K2CO3 (872 mg, 6.31 mmol), copper(I) chloride (31 mg, 0.32 mmol) and L-proline (73 mg, 0.63 mmol) in DMF (8 mL) was heated under argon to 110° C. for 24 h. The reaction mixture was cooled to RT and partitioned between water and DCM before being filtered through a celite plug. The layers were separated and the aqueous phase was re-extracted with DCM (2×). The combined organic phases were washed with brine, dried over Na2SO4, filtered and evaporated in vacuo to give the crude product that was purified by flash chromatography (eluting with a gradient of 50% to 100% EtOAc in hexane) to give the title compound as a white solid. LC-MS B: tR=0.51 min; [M+H]+=257.86.

Provenance & Evidence