1,2-Dimethoxyethane → HCID 25121515, 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, 200 mg, 0.49 mmol), 2-cyclohex-1-en-1-yl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (158 μl, 0.74 mmol), sodium carbonate (0.49 ml, 2M aqueous solution, 0.98 mmol) and tetrakis(triphenylphosphino)palladium(0) (57 mg, 0.05 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 to afford the title compound as a white solid (115 mg, 57%): 1H NMR (400 MHz, DMSO-d6) 8.60 (s, 1H), 7.78 (d, 2H), 7.49 (d, 2H), 7.17 (d, 2H), 7.08 (d, 2H), 6.67 (s, 1H), 6.23 (m, 1H), 5.37 (s, 2H), 2.41-2.37 (m, 2H), 2.28 (s, 3H), 2.27 (s, 3H), 2.22-2.17 (m, 2H), 1.77-1.70 (m, 2H), 1.64-1.59 (m, 2H); ES-MS m/z 410, HPLC RT (Method D) 3.48 min.

Provenance & Evidence