Potassium Carbonate → HCID 67243137, compound

Participants

Reaction Conditions

Reaction Steps

A 0.5-2 ml microwave vial was charged with potassium carbonate (59.8 mg, 0.433 mmol), 2-fluoropyridin-3-ylboronic acid (34.5 mg, 0.245 mmol) and AmPhos (5.11 mg, 7.21 μmol). A solution of (R)-2-amino-2′-morpholino-5H-spiro[oxazole-4,9′-xanthene]-7′-yl trifluoromethanesulfonate (70 mg, 0.144 mmol) in dioxane (841 μL) was added followed by water (120 μL). Rhe vial was sealed and heated in microwave reactor at 100° C. for 1 hr. Tetrakis(triphenylphosphine)palladium(0) (16.66 mg, 0.014 mmol) and 2-fluoropyridin-3-ylboronic acid (34.5 mg, 0.245 mmol) were added and the mixture was heated for 30 min at 110 C in the microwave reactor. The dark brown mixture was diluted with 3 ml of ethyl acetate, filtered through celite and concentrated. The mixture was purified by silica gel chromatography on 12 g RediSep column using 15-60% DCM/MeOH/NH4OH in DCM. The derived residue was then purified by reverse phase HPLC (15-90% MeCN in 0.1% aq. TFA) to afford (S)-2′-(2-fluoropyridin-3-yl)-7′-morpholino-5H-spiro[oxazole-4,9′-xanthen]-2-amine 2,2,2-trifluoroacetate as an off white solid. Found MS: MH+=441.

Provenance & Evidence