Cesium carbonate → HCID 86653490, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 3-bromo-9-(2-trimethylsilanylethoxymethyl)dipyrido[2,3-b;4′,3′-d]pyrrole-6-carbonitrile (1.53 g, 3.79 mmol), tert-butyl carbamate (888 mg, 7.58 mmol), and cesium carbonate (2.47 g, 7.58 mmol) were suspended in 1,4-dioxane (30 mL) degassed and purged with nitrogen three times. 4,5-bis(Diphenylphosphino)-9,9-dimethylxanthene (219 mg, 0.379 mmol) and tris(dibenzylideneacetone)dipalladium(0) (173 mg, 0.189 mmol) were added and the reaction mixture heated at 90° C. for 25 h. The cooled reaction mixture was pre-absorbed onto silica gel and purified by flash chromatography on silica (silica, 120 g column, Biotage, 10-60% EtOAc in heptane) to afford the title compound as a white-yellow solid (1.3 g, 80%). 1H NMR (400 MHz, DMSO-D6): 9.74 (s, 1H), 9.26 (s, 1H), 9.02 (s, 1H), 8.95 (s, 1H), 8.67 (d, J=2.4, 1H), 5.98 (s, 2H), 3.55 (t, J=7.9, 2H), 1.52 (s, 9H), 0.81 (t, J=7.9, 2H), −0.12-−0.23 (m, 9H).

Provenance & Evidence