1,1,1-Trifluoro-2,4-pentanedione → 2,2,2-Trifluoro-1-[4-(4-fluoro-phenyl)-6-methyl-thieno[2,3-b]pyridin-5-yl)-ethanone

HRID 133521Notes

Reaction equation

[NH2:1][C:2]1[S:3][CH:4]=[CH:5][C:6]=1[C:7]([C:9]1[CH:14]=[CH:13][C:12]([F:15])=[CH:11][CH:10]=1)=O.[F:16][C:17]([F:25])([F:24])[C:18](=[O:23])[CH2:19][C:20](=O)[CH3:21]>C(O)(=O)C.S(=O)(=O)(O)O>[F:16][C:17]([F:25])([F:24])[C:18]([C:19]1[C:7]([C:9]2[CH:14]=[CH:13][C:12]([F:15])=[CH:11][CH:10]=2)=[C:6]2[CH:5]=[CH:4][S:3][C:2]2=[N:1][C:20]=1[CH3:21])=[O:23]

Participants

Conditions

Temperature: 100 °C

Procedure

To a stirred solution of 30 mg (0.13 mmol) (2-amino-thiophen-3-yl)-(4-fluoro-phenyl)-methanone in 1 ml acetic acid was added 0.017 ml (0.13 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 15 minutes in a microwave and then concentrated in vacuo. Preparative HPLC (30% CH3CN/H20) afforded 8 mg (17%) 2,2,2-trifluoro-1-[4-(4-fluoro-phenyl)-6-methyl-thieno[2,3-b]pyridin-5-yl)-ethanone as a yellow oil. ES-MS m/e (%): 340 (M+H+, 100).

Workup

concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-afe464eb7436448181ae2363c949a676
Source dataset: uspto-grants-2008_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07390903B2

Reaction notes

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