Cesium carbonate → HCID 68516515, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 4-(1-(4-methoxybenzyl)-3-iodo-1H-pyrazolo[3,4-b]pyridin-4-yloxy)-3-fluorobenzenamine (0.30 g, 0.612 mmol; prepared as in Example 7, Step B), Cs2CO3 (0.299 g, 0.918 mmol), and 4-(morpholine-4-carbonyl)phenylboronic acid (0.151 g, 0.643 mmol) in DME (3 mL) was degassed under nitrogen for 10 minutes and tetrakistriphenylphosphinepalladium (0.035 g, 0.03 mmol) was added. The reaction mixture was heated at 85° C. for 15 hours. The precipitate was removed by filtration with a mixture of EtOAc and MeOH. The filtrate was concentrated and the crude material was purified by silica gel flash column chromatography (1% MeOH in CH2Cl2) to afford 39 mg (12%) of the desired product. LRMS (APCI pos) m/e 554.1 (M+1).

Provenance & Evidence