Acetylacetone → 1-(6-Methyl-2,4-diphenyl-thieno[2,3-b]pyridin-5-yl)-ethanone

HRID 133548Notes

Reaction equation

[NH2:1][C:2]1[S:3][C:4]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[CH:5][C:6]=1[C:7]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=O.[CH3:21][C:22](=O)[CH2:23][C:24](=[O:26])[CH3:25]>S(=O)(=O)(O)O.C(O)(=O)C>[CH3:21][C:22]1[N:1]=[C:2]2[S:3][C:4]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)=[CH:5][C:6]2=[C:7]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[C:23]=1[C:24](=[O:26])[CH3:25]

Participants

Conditions

Temperature: 100 °C

Procedure

To a stirred solution of 55 mg (0.197 mmol) (2-amino-5-phenyl-thiophen-3-yl)-phenyl-methanone-in-5 ml-acetic acid was added 0.016 ml (0.239 mmol) of 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 19 mg (28%) 1-(6-methyl-2,4-diphenyl-thieno[2,3-b]pyridin-5-yl)-ethanone as a light grey solid. ES-MS m/e (%): 344 (M+H+, 100).

Workup

concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-4918166fe412414688b550ec325eb7b1
Source dataset: uspto-grants-2008_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07390903B2

Reaction notes

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