Toluene → HCID 18693288, compound

Participants

Reaction Steps

A mixture of ethyl 5-(2-morpholin-4-ylethoxy)-1-(4-bromophenyl)pyrazole-4-carboxylate (0.25 g, 0.59 mmol), sodium carbonate (0.20 g, 1.77 mmol), tetrakis(triphenylphosphine) palladium (0) (0.12 g, 0.18 mmol) and 1-formylbenzeneboronic acid (0.10 g, 0.76 mmol) in a solution of toluene (10 mL), ethanol (1 mL) and water (1 mL) was stirred at reflux for 18 h. The reaction was diluted with water and extracted with ethyl acetate. The organic extract was washed with brine and dried (Na2SO4). After removing the solvent, flash chromatography of the residue (silica gel, 50% ethyl acetate/hexane) afforded the title compound as an oil (0.14 g, 66%). 1H NMR (250 MHz, CDCl3) d 9.98 (s, 1H), 8.01 (d, 1H), 7.92 (s, 1H), 7.85 (d, 2H), 7.62 (d, 1H), 7.46 (m, 4H), 4.65 (t, 2H), 4.35 (q, 2H), 3.56 (t, 4H), 2.68 (t, 2H), 2.38 (t, 4H), 1.38 (t, 3H). MS(ESI) m/e 450.4 [M+H]+.

Provenance & Evidence