Ethyl Acetate → ethyl 1-(4-fluorophenyl)-2-((2-(2,3,6-trifluorophenyl)propaN-2-yl)thio)-1H-imidazole-5-carboxylate

HRID 2368527Notes

Reaction equation

HRID 2368527 reaction equation
[F:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[C:4]([F:9])[C:3]=1[C:10](O)([CH3:12])[CH3:11].[F:14][C:15]1[CH:20]=[CH:19][C:18]([N:21]2[C:25]([C:26]([OH:28])=[O:27])=[CH:24][N:23]=[C:22]2[S:29]C(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=[CH:17][CH:16]=1.[CH3:49][CH2:50]OC(C)=O>C(Cl)Cl.[I-].[Zn+2].[I-]>[F:14][C:15]1[CH:16]=[CH:17][C:18]([N:21]2[C:25]([C:26]([O:28][CH2:49][CH3:50])=[O:27])=[CH:24][N:23]=[C:22]2[S:29][C:10]([C:3]2[C:4]([F:9])=[CH:5][CH:6]=[C:7]([F:8])[C:2]=2[F:1])([CH3:12])[CH3:11])=[CH:19][CH:20]=1

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 711174681-(4-fluorophenyl)-2-(tritylthio)-1H-imidazole-5-carboxylic acidHCID 833844992-(2,3,6-Trifluorophenyl)propan-2-ol

Product 1

HCID 71118251ethyl 1-(4-fluorophenyl)-2-((2-(2,3,6-trifluorophenyl)propaN-2-yl)thio)-1H-imidazole-5-carboxylate

Reagents, catalysts & solvents 2

HCID 9883512zinc(II)iodideCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-(2,3,6-trifluorophenyl)propan-2-ol (74) (0.73 g, 3.8 mmol) and ethyl 1-(4-fluorophenyl)-2-mercapto-1H-imidazole-5-carboxylate (6) (1.12 g, 4.2 mmol) in CH2Cl2 (5 mL) was added zinc iodide (1.7 g, 5.3 mmol) at room temperature. The mixture was stirred at room temperature overnight. The reaction was diluted with EtOAc and washed with 0.5 N NaOH, water, brine, dried over sodium sulfate, filtered and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel to afford ethyl 1-(4-fluorophenyl)-2-((2-(2,3,6-trifluorophenyl)propaN-2-yl)thio)-1H-imidazole-5-carboxylate. (75).

Workup

  1. washwashed with 0.5 N NaOH, water, brine
  2. dry with materialdried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by flash column chromatography on silica gel

Sources & evidence

ORD record
ord-74900ade3cad4aa8852859770f391fe9
Source dataset
uspto-grants-2014_04
Patent number
US08703776B2

Reaction notes

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