1,1,1-Trifluoro-2,4-pentanedione → 2,2,2-trifluoro-1-(2-methyl-4-phenyl-6,7-dihydro-5H-cyclopenta[4,5]thieno [2,3-b]pyridin-3-yl)-ethanone

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 50 mg (0.20 mmol) (2-amino-5,6-dihydro-4H-cyclopenta[b]thiophen-3-yl)-phenyl-methanone (the preparation of which is described in example 2) in 2 ml acetic acid was added 0.026 ml (0.20 mmol) of 1,1,1-trifluoro-pentane-2,4-dione and one drop of sulfuric acid. The mixture was then stirred at 100° C. for 10 minutes in a microwave and then concentrated in vacuo. Flash chromatography (heptane/ethyl acetate 20:1) afforded 20 mg (27%) 2,2,2-trifluoro-1-(2-methyl-4-phenyl-6,7-dihydro-5H-cyclopenta[4,5]thieno [2,3-b]pyridin-3-yl)-ethanone as an orange oil. ES-MS m/e (%): 362 (M+H+, 100).

Provenance & Evidence