Potassium Carbonate → HCID 53464881, compound

Participants

Reaction Steps

A vial was charged with (S)-2′-amino-3-((3-methyloxetan-3-yl)ethynyl)-5′H-spiro[chromeno[2,3-b]pyridine-5,4′-oxazole]-7-yl trifluoromethanesulfonate (92 mg, 0.186 mmol, prepared from the alcohol as described in Method CC6), 3-cyanophenylboronic acid (82 mg, 0.557 mmol), potassium carbonate (128 mg, 0.928 mmol), and Cl2Pd(dppf) (1.516 mg, 1.857 μmol). The vial was flushed with argon, then dioxane (928 μL) and water (0.5 mL) were added. The vial was sealed and placed in an 80° C. oil bath for 1.5 hours. An additional portion of catalyst (3 mg) was added and the mixture was returned to the 80° C. oil bath. Heating was continued for an additional 2 hours. The mixture was cooled to rt and was diluted with EtOAc (15 mL) and brine (20 mL). The layers were separated, and the aqueous layer was extracted with EtOAc (15 mL). The combined organic layers were dried over sodium sulfate, filtered, and evaporated. The residue was chromatographed on a 40-g Redi-Sep column, eluting with 0-50% of a 90:10:1 mix of CH2Cl2/MeOH/NH4OH in CH2Cl2 to give (S)-3-(2′-amino-3-((3-methyloxetan-3-yl)ethynyl)-5′H-spiro[chromeno[2,3-b]pyridine-5,4′-oxazole]-7-yl)benzonitrile as a pale, tan solid.

Provenance & Evidence