Piperidine → HCID 25121514, compound

Participants

Reaction Steps

A mixture of 4-(4-bromophenyl)-2-[5-methyl-1-(4-methylbenzyl)-1H-pyrazol-3-yl]-1,3-oxazole (Example 75, 150 mg, 0.37 mmol), piperidine (44 μl, 0.44 mmol), potassium phosphate (156 mg, 0.74 mmol), palladium(II) chloride (3.3 mg, 0.02 mmol) and 2-(dicyclohexylphosphino)-1,1′-biphenyl (9.7 mg, 0.03 mmol) in 1,2-dimethoxyethane (3 ml) was heated to reflux for 18 h. After cooling to rt, the mixture was filtered over a pad of celite. The filtrate was diluted with ethyl acetate and successively washed with 0.1 N aqueous HCl and water. The organic layer was dried (MgSO4), filtered and concentrated to dryness. The crude material was purified by preparative HPLC. The combined product fractions were then further purified by flash chromatography (silica) eluting with cyclohexane/ethyl acetate 5:1 to afford the title compound as a white solid (17 mg, 11%): 1H NMR (400 MHz, DMSO-d6) δ 8.42 (s, 1H), 7.63 (d, 2H), 7.17 (d, 2H), 7.08 (d, 2H), 6.98 (d, 2H), 6.65 (s, 1H), 5.35 (s, 2H), 3.19 (m, 4H), 2.28 (s, 6H), 1.64-1.52 (m, 6H); ES-MS m/z 413, HPLC RT (Method D) 2.65 min.

Provenance & Evidence