Sodium Carbonate → HCID 178491066, compound

Participants

Reaction Conditions

Reaction Steps

trans-4-(3-Chloropyrazin-2-yloxy)-N,N-bis(4-methoxybenzyl)cyclohexanamine (0.810 g, 1.73 mmol), 2-(3,6-dihydro-2H-pyran-4-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (0.455 g, 2.16 mmol), and tetrakis(triphenylphosphine)palladium(0) (0.100 g, 0.087 mmol) were mixed in DME (2 mL) under a nitrogen atmosphere. Sodium carbonate (2.60 mL, 5.19 mmol, 2 M in water) was added via syringe, and the reaction mixture was then heated to 80° C. and stirred for 5 h. The mixture was cooled to RT and partitioned between EtOAc and water. The layers were separated, and the aqueous layer was extracted with EtOAc (2×). The extracts were combined, dried over magnesium sulfate, filtered, and concentrated. The resulting crude product was purified by silica gel chromatography to give trans-4-(3-(3,6-dihydro-2H-pyran-4-yl)pyrazin-2-yloxy)-N,N-bis(4-methoxybenzyl)cyclohexanamine as a light yellow solid.

Provenance & Evidence