Chloroacetone → 1-(2'-amino-7-bromo-5'H-spiro[chromeno[2,3-b]pyridine-5,4'-oxazole]-3-yloxy)propan-2-one

Participants

Reaction Steps

A solution of 2′-amino-7-bromo-5′H-spiro[chromeno[2,3-b]pyridine-5,4′-oxazol]-3-ol (0.570 g, 1.637 mmol) in 5 mL DMF was treated with potassium carbonate (0.283 g, 2.047 mmol) and was allowed to stir at RT for 15 minutes. The reaction mixture was then cooled to 0° C. and 1-chloropropan-2-one (0.151 g, 1.637 mmol) was added as a solution in 1 mL THF. After stirring for one hour the reaction mixture was allowed to warm to RT and stir for 4 hours. The reaction mixture was poured into 1:1 water/brine, extracted with EtOAc (3×25 mL). The combined organics were dried over MgSO4 and concentrated. Purification of the crude residue by column chromatography provided 1-(2′-amino-7-bromo-5′H-spiro[chromeno[2,3-b]pyridine-5,4′-oxazole]-3-yloxy)propan-2-one. MS m/z=404.0 [M+H].

Provenance & Evidence