2-Methyl-3-butyn-2-ol → HCID 67387634, compound

Participants

Reaction Conditions

Reaction Steps

A vial charged with (S)-2-amino-7′-bromo-3′-fluoro-5H-spiro[oxazole-4,9′-xanthen]-2′-ol (0.225 g, 0.616 mmol), Pd(PPh3)4 (0.071 g, 0.062 mmol), and copper(i) iodide (0.012 g, 0.062 mmol), was treated with 3 mL DMF followed by DIPA (1.317 mL, 9.24 mmol). The solution was purged with argon for 2 minutes then 2-methylbut-3-yn-2-ol (0.301 mL, 3.08 mmol) was added and the vial was sealed and heated to 80° C. overnight. The reaction mixture was poured into saturated NH4Cl (50 mL) and was extracted with EtOAc (3×25 mL). The combined organics were washed with brine, dried over MgSO4 and concentrated. Purification of the crude residue by column chromatography [0-100% (9:1:0.1—CH2Cl2:MeOH:NH4OH)/CH2Cl2] provided (R)-2-amino-3′-fluoro-7′-(3-hydroxy-3-methylbut-1-ynyl)-5H-spiro[oxazole-4,9′-xanthen]-2′-ol. MS m/z=369.3 [M+H].

Provenance & Evidence