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

HRID 2368474Notes

Reaction equation

HRID 2368474 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12]([C:13](N(OC)C)=[O:14])=[CH:11][N:10]=[C:9]2[S:19][CH2:20][C:21]2[C:26]([F:27])=[CH:25][CH:24]=[C:23]([F:28])[C:22]=2[F:29])=[CH:4][CH:3]=1.FC1C=CC(N2[C:41]([C:42](O)=[O:43])=CN=C2SC(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=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:43][CH2:42][CH3:41])=[O:14])=[CH:11][N:10]=[C:9]2[S:19][CH2:20][C:21]2[C:26]([F:27])=[CH:25][CH:24]=[C:23]([F:28])[C:22]=2[F:29])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 5190612,3,6-Trifluorobenzyl bromideHCID 711174681-(4-fluorophenyl)-2-(tritylthio)-1H-imidazole-5-carboxylic acidHCID 866775411-(4-Fluorophenyl)-N-methoxy-N-methyl-2-((2,3,6-trifluorobenzyl)thio)-1H-imidazole-5-carboxamide

Product 1

HCID 71117421Ethyl 1-(4-fluorophenyl)-2-((2,3,6-trifluorobenzyl)thio)-1H-imidazole-5-carboxylate

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Ethyl 1-(4-fluorophenyl)-2-((2,3,6-trifluorobenzyl)thio)-1H-imidazole-5-carboxylate (10) was prepared in a similar manner as that described for the synthesis of compound 9 using ethyl 1-(4-fluorophenyl)-2-mercapto-1H-imidazole-5-carboxylate (6) (202 mg, 0.76 mmol), 2,3,6-trifluorobenzyl bromide (0.1 mL, 0.76 mmol), and potassium carbonate (125.9 mg, 0.91 mmol) in acetone (3 mL).

Sources & evidence

ORD record
ord-a3d1082ed82d44c696bdcce801d97a5d
Source dataset
uspto-grants-2014_04
Patent number
US08703776B2

Reaction notes

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