Acetylacetone → (2-Methyl-4-phenyl-benzo[4,5]thieno[2,3-b]pyridin-3-yl)-ethanone

HRID 133505Notes

Reaction equation

[NH2:1][C:2]1[S:6][C:5]2[CH:7]=[CH:8][CH:9]=[CH:10][C:4]=2[C:3]=1[C:11]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=O.[CH3:19][C:20](=O)[CH2:21][C:22](=[O:24])[CH3:23]>C(O)(=O)C.S(=O)(=O)(O)O>[CH3:19][C:20]1[N:1]=[C:2]2[S:6][C:5]3[CH:7]=[CH:8][CH:9]=[CH:10][C:4]=3[C:3]2=[C:11]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:21]=1[C:22](=[O:24])[CH3:23]

Participants

Conditions

Temperature: 100 °C

Procedure

To a stirred solution of 32 mg (0.13 mmol) (2-amino-benzo[b]thiophen-3-yl)-phenyl-methanone in 2 ml acetic acid was added 0.09 ml (0.13 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. Flash chromatography (heptane/ethyl acetate 6:1) afforded 21 mg (52%) (2-methyl-4-phenyl-benzo[4,5]thieno[2,3-b]pyridin-3-yl)-ethanone as a light yellow solid. ES-MS m/e (%): 318 (M+H+, 100).

Workup

concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-214c714b92f648cf90bc7eaa904e29b6
Source dataset: uspto-grants-2008_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07390903B2

Reaction notes

Loading…