Potassium Carbonate → Ethyl 1-(4-fluorophenyl)-4-methyl-2-((2,3,6-trifluorobenzyl)thio)-1H-imidazole-5-carboxylate

HRID 2368516Notes

Reaction equation

HRID 2368516 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[S:18][CH2:19][C:20]2[C:25]([F:26])=[CH:24][CH:23]=[C:22]([F:27])[C:21]=2[F:28])=[CH:4][CH:3]=1.F[C:30]1C=CC(N2C(C(OCC)=O)=C(C)N=C2S)=CC=1.FC1C(F)=CC=C(F)C=1CBr.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[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])=[C:11]([CH3:30])[N:10]=[C:9]2[S:18][CH2:19][C:20]2[C:25]([F:26])=[CH:24][CH:23]=[C:22]([F:27])[C:21]=2[F:28])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 5190612,3,6-Trifluorobenzyl bromideHCID 71117421Ethyl 1-(4-fluorophenyl)-2-((2,3,6-trifluorobenzyl)thio)-1H-imidazole-5-carboxylateHCID 178469260HCID 178469260, compound

Product 1

HCID 71117617Ethyl 1-(4-fluorophenyl)-4-methyl-2-((2,3,6-trifluorobenzyl)thio)-1H-imidazole-5-carboxylate

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Ethyl 1-(4-fluorophenyl)-4-methyl-2-((2,3,6-trifluorobenzyl)thio)-1H-imidazole-5-carboxylate (58) was prepared in a similar manner as that described for the synthesis of compound 10 using 1-(4-fluorophenyl)-2-mercapto-4-methyl-1H-imidazole-5-carboxylate (57) (500 mg, 1.78 mmol), 2,3,6-trifluorobenzyl bromide (560 mg, 2.49 mmol) and potassium carbonate (736 mg, 6 mmol) in acetone (18 mL).

Sources & evidence

ORD record
ord-603e08af8eec4d7abb5372744cf8dfb9
Source dataset
uspto-grants-2014_04
Patent number
US08703776B2

Reaction notes

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