Sodium Carbonate → HCID 58466261, compound

Participants

Reaction Conditions

Reaction Steps

Resealable tube was charged with (S)-2-amino-4′-fluoro-2′-(2-oxopyrolidin-1-yl)-5H-spiro[oxazole-4,9′-xanthene]-7′-yl trifluoromethanesulfonate (130 mg, 0.26 mmol), tetrakis(triphenylphosphine)palladium(0) (30.0 mg, 0.026 mmol), pyridin-3-ylboronic acid (51.0 mg, 0.42 mmol). DMF (1.3 mL) and sodium carbonate (2M, 0.4 mL, 0.8 mmol) were added and the mixture was sealed and heated at 90° C. for 2 h. The mixture was partitioned between water (1 mL) and ethyl acetate (5 mL), organic layer was washed with water, concentrated and purified by FC on 12 g RediSep Gold column using 10-80% DCM/MeOH/NH4OH 90:10:1 in DCM. The fractions containing pure product by TLC were combined and concentrated to afford (S)-1-(2-amino-5′-fluoro-2′-(pyridin-3-yl)-5H-spiro[oxazole-4,9′-xanthene]-7′-yl)pyrolidin-2-one.

Provenance & Evidence