1,1,1-Trifluoro-2,4-pentanedione → HCID 11646575, compound

HRID 133513Notes

Reaction equation

[NH2:1][C:2]1[S:6][C:5]2[CH2:7][CH2:8][CH2:9][C:4]=2[C:3]=1[C:10]([C:12]1[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=1)=O.[F:19][C:20]([F:28])([F:27])[C:21](=[O:26])[CH2:22][C:23](=O)[CH3:24]>C(O)(=O)C.S(=O)(=O)(O)O>[F:19][C:20]([F:28])([F:27])[C:21]([C:22]1[C:10]([C:12]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=2)=[C:3]2[C:4]3[CH2:9][CH2:8][CH2:7][C:5]=3[S:6][C:2]2=[N:1][C:23]=1[CH3:24])=[O:26]

Participants

Conditions

Temperature: 100 °C

Procedure

To a stirred solution of 50 mg (0.19 mmol) (2-amino-5,6-dihydro-4H-cyclopenta[b]thiophen-3-yl)-(4-fluoro-phenyl)-methanone in 2 ml acetic acid was added 0.024 ml (0.19 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 9:1) afforded 10 mg (14%) 2,2,2-trifluoro-1-[4-(4-fluoro-phenyl)-2-methyl-6,7-dihydro-5H-cyclopenta[4,5]thieno[2,3-b]pyridin-3-yl)-ethanone as a light brown solid. ES-MS m/e (%): 380 (M+H+, 100).

Workup

concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-c6fcdd697e814c5a88e4327fa89a9369
Source dataset: uspto-grants-2008_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07390903B2

Reaction notes

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