1,1,1-Trifluoro-2,4-pentanedione → HCID 11544922, compound

HRID 133519

Reaction equation

HRID 133519 reaction equation
[NH2:1][C:2]1[S:3][C:4]([Cl:15])=[CH:5][C:6]=1[C:7]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=O.[F:16][C:17]([F:25])([F:24])[C:18](=[O:23])[CH2:19][C:20](=O)[CH3:21]>C(O)(=O)C.S(=O)(=O)(O)O>[Cl:15][C:4]1[S:3][C:2]2=[N:1][C:20]([CH3:21])=[C:19]([C:18](=[O:23])[C:17]([F:25])([F:24])[F:16])[C:7]([C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=3)=[C:6]2[CH:5]=1

Participants

5

Reactant 2

HCID 739431,1,1-Trifluoro-2,4-pentanedioneHCID 16640283(2-Amino-5-chloro-thiophen-3-yl)-phenyl-methanone

Product 1

HCID 11544922HCID 11544922, compoundYield 23%

Reagents, catalysts & solvents 2

HCID 1118Sulfuric AcidCatalystHCID 176Acetic AcidSolvent

Conditions

Temperature
70 °C

Procedure

To a stirred solution of 30 mg (0.13 mmol) (2-amino-5-chloro-thiophen-3-yl)-phenyl-methanone in 2 ml acetic acid was added 0.016 ml (0.13 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. Preparative HPLC (30% CE-CN/H20) afforded 10 mg (23%) 1-(2-chloro-6-methyl-4-phenyl-thieno[2,3-b]pyridin-5-yl)-2,2,2-trifluoro-ethanone as a light brown solid. ES-MS m/e (%): 356 (M+H+, 100).

Workup

  1. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-ab232513225c47fca077c1f40b2a7bec
Source dataset
uspto-grants-2008_06
Patent number
US07390903B2

Linked notes

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