Acetylacetone → HCID 11543896, compound

HRID 133510Notes

Reaction equation

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

Participants

Conditions

Temperature: 100 °C

Procedure

To a stirred solution of 70 mg (0.30 mmol) (2-Amino-4,5-dimethyl-thiophen-3-yl)-phenyl-methanone in 2 ml acetic acid was added 0.02 ml (0.30 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 10 mg (11%) 1-(2,3,6-trimethyl-4-phenyl-thieno[2,3-b]pyridine-5-yl)-ethanone as an orange solid. ES-MS m/e (%): 296 (M+H+, 100).

Workup

concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-317dbb5f44174e9eac6b57e4f5604794
Source dataset: uspto-grants-2008_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07390903B2

Reaction notes

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