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

HRID 133526Notes

Reaction equation

HRID 133526 reaction equation
[NH2:1][C:2]1[S:3][C:4]([Cl:16])=[CH:5][C:6]=1[C:7]([C:9]1[CH:14]=[CH:13][C:12]([F:15])=[CH:11][CH:10]=1)=O.[F:17][C:18]([F:26])([F:25])[C:19](=[O:24])[CH2:20][C:21](=O)[CH3:22]>C(O)(=O)C.S(=O)(=O)(O)O>[Cl:16][C:4]1[S:3][C:2]2=[N:1][C:21]([CH3:22])=[C:20]([C:19](=[O:24])[C:18]([F:26])([F:25])[F:17])[C:7]([C:9]3[CH:14]=[CH:13][C:12]([F:15])=[CH:11][CH:10]=3)=[C:6]2[CH:5]=1

Participants

5

Reactant 2

HCID 739431,1,1-Trifluoro-2,4-pentanedioneHCID 68896462(2-Amino-5-chloro-thiophen-3-yl)-(4-fluoro-phenyl)-methanone

Product 1

HCID 115959011-[2-Chloro-4-(4-fluoro-phenyl)-6-methyl-thieno[2,3-b]pyridin-5-yl)-2,2,2-trifluoro-ethanoneYield 11.3%

Reagents, catalysts & solvents 2

HCID 1118Sulfuric AcidCatalystHCID 176Acetic AcidSolvent

Conditions

Temperature
70 °C

Procedure

To a stirred solution of 50 mg (0.19 mmol) (2-amino-5-chloro-thiophen-3-yl)-(4-fluoro-phenyl)-methanone in 2 ml acetic acid was added 0.025 ml (0.19 mmol) of 1,1,1-trifluoro-pentane-2,4-dione and one drop of sulfuric acid. The mixture was then stirred at 70° C. for 10 minutes in a microwave and then concentrated in vacuo. Flash chromatography (heptane/ethyl acetate 9:1) afforded 8 mg (11%) 1-[2-chloro-4-(4-fluoro-phenyl)-6-methyl-thieno[2,3-b]pyridin-5-yl)-2,2,2-trifluoro-ethanone as an orange oil. ES-MS m/e (%): 374 (M+H+, 100).

Workup

  1. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-29a819e44d11484c84357a8346dae3dc
Source dataset
uspto-grants-2008_06
Patent number
US07390903B2

Reaction notes

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