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

HRID 133517

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][CH:12]=[CH:11][CH:10]=1)=O.[F:15][C:16]([F:24])([F:23])[C:17](=[O:22])[CH2:18][C:19](=O)[CH3:20]>C(O)(=O)C.S(=O)(=O)(O)O>[F:15][C:16]([F:24])([F:23])[C:17]([C:18]1[C:7]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[C:6]2[CH:5]=[CH:4][S:3][C:2]2=[N:1][C:19]=1[CH3:20])=[O:22]

Participants

Conditions

Temperature: 100 °C

Procedure

To a stirred solution of 50 mg (0.24 mmol) (2-amino-thiophen-3-yl)-phenyl-methanone in 2 ml acetic acid was added 0.031 ml (0.24 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. Preparative HPLC (30% CH3CN/H20) afforded 13 mg (17%) 2,2,2-trifluoro-1-(6-methyl-4-phenyl-thieno[2,3-b]pyridin-5-yl)-ethanone as a yellow oil. ES-MS m/e (%): 322 (M+H+, 100).

Workup

concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-fe41fcf64da04855b16fce2bcf085606
Source dataset: uspto-grants-2008_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07390903B2

Linked notes

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