ethyl 1-(4-fluorophenyl)-2-(2,3,6-trifluorophenethyl)-1H-imidazole-5-carboxylate → (2-(trifluoromethyl)phenethyl)-1H-imidazole-5-carboxylate

HRID 2368507Notes

Reaction equation

HRID 2368507 reaction equation
FC1C=CC([N:8]2[C:12]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:11][N:10]=[C:9]2CCC2C(F)=CC=C(F)C=2F)=CC=1.FC1C=CC(N2C(C(OCC)=O)=CN=C2C#C[C:48]2[CH:53]=[CH:52][CH:51]=[CH:50][C:49]=2[C:54]([F:57])([F:56])[F:55])=CC=1>[Pd].C(OCC)(=O)C.C(O)C>[F:55][C:54]([F:57])([F:56])[C:49]1[CH:50]=[CH:51][CH:52]=[CH:53][C:48]=1[CH2:17][CH2:16][O:15][C:13]([C:12]1[NH:8][CH:9]=[N:10][CH:11]=1)=[O:14]

Participants

5

Reactant 2

HCID 71117630ethyl 1-(4-fluorophenyl)-2-(2,3,6-trifluorophenethyl)-1H-imidazole-5-carboxylateHCID 71117657Ethyl 1-(4-fluorophenyl)-2-((2-(trifluoromethyl)phenyl)ethynyl)-1H-imidazole-5-carboxylate

Product 1

HCID 86677553(2-(trifluoromethyl)phenethyl)-1H-imidazole-5-carboxylate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21584252Ethanol ethylacetateSolvent

Procedure

Ethyl 1-(4-fluorophenyl)-2-((2-(trifluoromethyl)phenethyl)-1H-imidazole-5-carboxylate (47) was prepared in a similar manner as that described for the synthesis of compound 18 using ethyl 1-(4-fluorophenyl)-2-((2-(trifluoromethyl)phenyl)ethynyl)-1H-imidazole-5-carboxylate (46) (651 mg, 1.62 mmol), Pd/C (10% Degussa type, 65 mg), and ethyl acetate/ethanol (1:2) (61 mL).

Sources & evidence

ORD record
ord-5f8058ea65d741de961eb8fe171fb7e6
Source dataset
uspto-grants-2014_04
Patent number
US08703776B2

Reaction notes

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