Acetylacetone → 3-acetyl-2-methyl-4-phenyl-5,8-dihydro-6H-9-thia-1,7-diaza-fluorene-7-carboxylic acid tert-butyl ester

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 0.50 g (1.39 mmol) 2-amino-3-benzoyl-4,7-dihydro-5H-thieno[2,3-c]pyridine-6-carboxylic acid tert-butyl ester in 6 ml acetic acid was added 0.19 ml (1.89 mmol) of pentane-2,4-dione and two drops of sulfuric acid. The mixture was then stirred at 100° C. for 25 minutes in a microwave and then concentrated in vacuo. Flash chromatography (heptane/ethyl acetate 4:1) afforded 70 mg (12%) 3-acetyl-2-methyl-4-phenyl-5,8-dihydro-6H-9-thia-1,7-diaza-fluorene-7-carboxylic acid tert-butyl ester as a yellow oil. ES-MS m/e (%): 423 (M+H+, 100).

Provenance & Evidence