Sodium Carbonate → 4-Phenoxyphenylboronic acid

Participants

Reaction Conditions

Reaction Steps

A mixture of 3-bromo-1-cyclopentyl-1H-pyrrolo [2,3-d]pyridazin-4-amine (0.057 g, 0.178 mmol), 4-phenoxyphenyl boronic acid (0.057 g, 0.266 mmol), sodium carbonate (0.062 g, 0.588 mmol) and tetrakis(triphenylphosphine)palladium(0) (12 mg, 0.011 mmol) in ethylene glycol dimethyl ether (3 mL) and water (1.5 mL) was heated at 85° C. under an atmosphere of nitrogen for 2.5 hours. The mixture was cooled to ambient temperature and the solvent evaporated under reduced pressure. The residue was purified by preparative reverse phase HPLC to give the title compound contaminated with 4-phenoxyphenyl boronic acid. The residue was partitioned between dichloromethane and 5 N aqueous sodium hydroxide. The organic layer was dried over magnesium sulfate, filtered and the filtrate evaporated to give the title compound (14 mg, 21%); 1H NMR (DMSO-d6, 400 MHz) δ 8.98 (s, 1H), 7.68 (s, 1H),, 7.50 (d, 2H), 7.40 (t, 2H), 7.17 (t, 1H), 7.09 (m, 4H), 5.76 (bs, 2H), 5.01 (m, 1H), 2.19 (m, 2H), 1.91 (m, 2H), 1.71 (m, 2H); 5%–100% acetonitrile-0.05 M ammonium acetate over 25 min, 1 mL/min) tr20.60 min.; LC/MS: MH+ 371.2.

Provenance & Evidence