Potassium Carbonate → HCID 86727595, compound

Participants

Reaction Conditions

Reaction Steps

To a mixture of 4-[7-bromo-4-methyl-3-oxo-2-(2-trimethylsilanyl-ethoxymethyl)-2,3,4,10-tetrahydro-9-oxa-1,2,4a-triaza-phenanthren-6-yl]-piperazine-1-carboxylic acid tert-butyl ester (0.31 g, 0.508 mmol), (2-fluorophenyl)boronic acid (0.107 g, 0.762 mmol), potassium carbonate (0.140 g, 1.015 mmol) in dioxane (12 mL) and water (2 mL) was added PdCl2(dppf)-CH2Cl2 adduct (0.041 g, 0.051 mmol) and the reaction mixture was heated at 90° C. overnight. The reaction mixture was cooled to ambient temperature and concentrated in vacuo. The residue was purified by column chromatography on silica gel (eluting with 3-15% EtOAc in petroleum ether) to give 4-[7-(2-fluoro-phenyl)-4-methyl-3-oxo-2-(2-trimethylsilanyl-ethoxymethyl)-2,3,4,10-tetrahydro-9-oxa-1,2,4a-triaza-phenanthren-6-yl]-piperazine-1-carboxylic acid tert-butyl ester (0.22 g, 69%) as a white solid. 1H NMR (400 MHz, CDCl3) δ 7.40 (m, 1H), 7.32 (m, 1H), 7.21-7.09 (m, 2H), 6.95 (s, 1H), 6.61 (s, 1H), 5.19-5.07 (m, 1H), 4.76 (q, J=6.8 Hz, 1H), 4.72-4.57 (d, J=13.2 Hz, 2H), 3.71-3.64 (m, 2H), 3.25 (m, 4H), 2.71 (t, J=4.8 Hz, 4H), 1.52 (d, J=6.8 Hz, 3H), 1.44 (s, 9H), 1.04-0.93 (m, 2H), 0.05-0.02 (m, 9H)

Provenance & Evidence