Cesium fluoride → HCID 118020586, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of (±)-(2-{[3-(4-fluorophenyl)-1H-pyrazol-1-yl]methyl}-1,3-oxazinan-3-yl)(2-iodo-5-methylphenyl)methanone obtained in Reference Example 23 (0.19 g, 0.38 mmol) and (tributylstannanyl)pyrimidine (0.15 mL, 0.46 mmol) in toluene (4 mL), Pd(PPh3)4 (0.044 g, 0.04 mmol), copper iodide (0.0070 g, 0.040 mmol) and cesium fluoride (0.12 g, 0.76 mmol) were added, and the resulting mixture was stirred with heating for 0.5 hours at 130° C. under irradiation of microwave. An aqueous solution of potassium fluoride was added to the reaction mixture, followed by extraction with CHCl3. The organic layer was washed with an aqueous solution of potassium fluoride, water and a saturated aqueous solution of sodium chloride. The organic layer was dried over Na2SO4, the drying agent was filtered off, and then concentrated under reduced pressure. The obtained residue was purified by column chromatography (HP-Sil 10 g, hexane/EtOAc=80/20 to 0/100) (KP-NH 12 g, hexane/EtOAc=80/20 to 0/100) to obtain the racemic mixture of title compound (0.099 g) (colorless oil). The obtained racemic mixture was divided using a semi-preparative column based on the racemic compound analysis conditions described earlier (condition 4, Rt1=3.9 min, Rt2=13.7 min) to obtain the title compound (0.036 g) having a short relative retention time (Rt1=3.9 min) (colorless oil).

Provenance & Evidence