Potassium Carbonate → HCID 86658462, compound

Participants

Reaction Conditions

Reaction Steps

A solution of potassium acetate (0.210 g, 2.140 mmol), PdCl2(dppf)-CH2Cl2 adduct (0.022 g, 0.027 mmol), (S)-2′-amino-3-((3-methyloxetan-3-yl)ethynyl)-5′H-spiro[chromeno[2,3-b]pyridine-5,4′-oxazole]-7-yl trifluoromethanesulfonate (0.265 g, 0.535 mmol), and bis(pinacolato)diboron (0.143 g, 0.562 mmol) in 5 mL DMF was heated to 100° C. for 3 hours. Pd(PPh3)4 (0.031 g, 0.027 mmol) was added, followed by 3-bromo-4-fluoropyridine (0.141 g, 0.802 mmol), potassium carbonate (0.296 g, 2.140 mmol), and 2 mL water. The reaction mixture was capped with argon and was heated to 100° C. for 2 hours. After cooling to RT, the reaction mixture was diluted with EtOAc and was washed sequentially with water and brine. The organics were dried over MgSO4 and concentrated. Purification of the crude residue by column chromatography [0-100% (9:1 CH2Cl2:MeOH)/CH2Cl2] then HPLC (10-90% MeCN/H2O) provided (S)-7-(4-fluoropyridin-3-yl)-3-(3-methyloxetan-3-yl)ethynyl)-5′H-spiro[chromeno[2,3-b]pyridine-5,4′-oxazol]-2′-amine. MS m/z=443.0 [M+H].

Provenance & Evidence