2-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenyl → ethyl 5-(6-fluoro-2-methyl-3-((1-methyl-cyclopropyl)amino)quinoxalin-5-yl)-2-methyl-1H-pyrrole-3-carboxylate

Participants

Reaction Steps

A mixture of Xphos (Strem Chemicals, 0.169 g, 0.355 mmol), Pd2dba3 (Frontier Scientific, 0.162 g, 0.177 mmol), potassium phosphate tribasic monohydrate (Fluka, 2.450 g, 10.64 mmol), 8-bromo-7-fluoro-3-methyl-N-(1-methylcyclopropyl)quinoxalin-2-amine (610a) (0.880 g, 2.84 mmol), ethyl 2-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrole-3-carboxylate (417a) (0.99 g, 3.55 mmol) in dioxane (10.32 mL) and water (3.87 mL) was microwaved to 110° C. for 30 min. Reaction mixture was separated into two biphasic layers. The organic layer was loaded onto a silica gel samplet. Purification by biotage (0-100% EtOAc/hexanes) produced ethyl 5-(6-fluoro-2-methyl-3-((1-methylcyclopropyl)amino)quinoxalin-5-yl)-2-methyl-1H-pyrrole-3-carboxylate (417b) (0.555 g, 1.451 mmol, 41% yield). m/z (ESI, +ve) 383.1 (M+H).

Provenance & Evidence