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

HRID 2368527
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HRID 2368527 반응식
[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
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 9883512zinc(II)iodide촉매
HCID 6344
Dichloromethane
용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-74900ade3cad4aa8852859770f391fe9
출처 데이터셋
uspto-grants-2014_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08703776B2

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