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

HRID 2368504Notes

Reaction equation

HRID 2368504 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:11][N:10]=[C:9]2[CH2:18][CH2:19][C:20]2[C:25](F)=[CH:24][CH:23]=[C:22](F)[C:21]=2[F:28])=[CH:4][CH:3]=1.ClC1C=CC=C(F)C=1C#CC1N(C2C=CC(F)=CC=2)C(C(OCC)=O)=CN=1>[Pd].C(OCC)(=O)C.C(O)C>[F:28][C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=1[CH2:19][CH2:18][C:9]1[N:8]([C:5]2[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=2)[C:12]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:11][N:10]=1

Participants

5

Reactant 2

HCID 71117630ethyl 1-(4-fluorophenyl)-2-(2,3,6-trifluorophenethyl)-1H-imidazole-5-carboxylateHCID 71119630ethyl 2-((2-chloro-6-fluorophenyl)ethynyl)-1-(4-fluorophenyl)-1H-imidazole-5-carboxylate

Product 1

HCID 71117902Ethyl 2-(2-fluorophenethyl)-1-(4-fluorophenyl)-1H-imidazole-5-carboxylate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21584252Ethanol ethylacetateSolvent

Procedure

Ethyl 2-(2-fluorophenethyl)-1-(4-fluorophenyl)-1H-imidazole-5-carboxylate (44) was prepared in a similar manner as that described for the synthesis of compound 18 using ethyl 2-((2-chloro-6-fluorophenyl)ethynyl)-1-(4-fluorophenyl)-1H-imidazole-5-carboxylate (42) (236 mg, 0.61 mmol), Pd/C (10% Degussa type, 23 mg), and ethyl acetate/ethanol (1:2) (61 mL).

Sources & evidence

ORD record
ord-bd44384b30a14fd4bd16c7becebac200
Source dataset
uspto-grants-2014_04
Patent number
US08703776B2

Reaction notes

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