Pyrazole → HCID 118117606, compound

Participants

Reaction Steps

A mixture of (R)-5-(3-iodo-4-methoxy-benzyl)-morpholin-3-one C-7 (60 mg, 0.17 mmol), pyrazole (18 mg, 0.30 mmol), K2CO3 (48 mg, 0.35 mmol), copper(I) chloride (1.7 mg, 0.02 mmol) and L-proline (4 mg, 0.04 mmol) in DMF (1 mL) was heated under argon to 110° C. for 168 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 (Biotage SP1, 10 g SNAP-cartridge eluting with 95:5 DCM:MeOH) to give the title compound as a brown oil. LC-MS B: tR=0.53 min; [M+H]+=288.16.

Provenance & Evidence