1,1,1-Trifluoro-2,4-pentanedione → 2,2,2-Trifluoro-1-[4-(4-methoxy-phenyl)-2-methyl-5,6,7,8-tetrahydro-benzo[4,5]thieno[2,3-b]pyridin-3-yl)-ethanone

HRID 133499Notes

Reaction equation

HRID 133499 reaction equation
[NH2:1][C:2]1[S:6][C:5]2[CH2:7][CH2:8][CH2:9][CH2:10][C:4]=2[C:3]=1[C:11]([C:13]1[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=1)=O.[F:21][C:22]([F:30])([F:29])[C:23](=[O:28])[CH2:24][C:25](=O)[CH3:26]>C(O)(=O)C.S(=O)(=O)(O)O>[F:21][C:22]([F:30])([F:29])[C:23]([C:24]1[C:11]([C:13]2[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=2)=[C:3]2[C:4]3[CH2:10][CH2:9][CH2:8][CH2:7][C:5]=3[S:6][C:2]2=[N:1][C:25]=1[CH3:26])=[O:28]

Participants

5

Reactant 2

HCID 739431,1,1-Trifluoro-2,4-pentanedioneHCID 7590663-(4-Methoxybenzoyl)-4,5,6,7-tetrahydro-1-benzothiophen-2-amine

Product 1

HCID 116471152,2,2-Trifluoro-1-[4-(4-methoxy-phenyl)-2-methyl-5,6,7,8-tetrahydro-benzo[4,5]thieno[2,3-b]pyridin-3-yl)-ethanoneYield 26.1%

Reagents, catalysts & solvents 2

HCID 1118Sulfuric AcidCatalystHCID 176Acetic AcidSolvent

Conditions

Temperature
100 °C

Procedure

To a stirred solution of 50 mg (0.17 mmol) (2-amino-4,5,6,7-tetrahydro-benzo[b]thiophen-3-yl)-(4-methoxy-phenyl)-methanone in 1.5 ml acetic acid was added 0.021 ml (0.18 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. Flash chromatography (heptane/ethyl acetate 9:1) afforded 18 mg (25%) 2,2,2-trifluoro-1-[4-(4-methoxy-phenyl)-2-methyl-5,6,7,8-tetrahydro-benzo[4,5]thieno[2,3-b]pyridin-3-yl)-ethanone as a yellow oil. ES-MS m/e (%): 406 (M+H+, 100).

Workup

  1. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-8b256792afa8407d83a51f4a6e04542c
Source dataset
uspto-grants-2008_06
Patent number
US07390903B2

Reaction notes

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