Sodium Carbonate → HCID 118274412, compound

Participants

Reaction Steps

To a mixture of Example 5F (500 mg, 1.404 mmol), 4-fluoro-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (399 mg, 1.684 mmol) and dichlorobis(triphenylphosphine)palladium (II) (99 mg, 0.14 mmol) in 7:3:2 1,2-dimethoxyethane/water/ethanol (14 mL) was added 2.45 mL 2M aqueous sodium carbonate. The suspension was stirred at room temperature for a few seconds and then stirred in a microwave reactor (Biotage Initiator) at 150° C. for 30 minutes. The mixture was partitioned between ethyl acetate and brine and the organic phase was concentrated. The residue was stirred in 2% methanol in methylene chloride and the solid was collected by filtration to provide the title compound. The mother liquor was purified by flash chromatography on silica gel (Teledyne CombiFlash Rf, 0-15% methanol in dichloromethane) to provide additional title compound. MS (ESI+) m/z 387 (M+H)+.

Provenance & Evidence