Methyl iodide → 5-(4-fluorobenzyl)-3-{(E)-2-[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl]vinyl}-1-methyl-1H-[1,2,4]triazole

HRID 1009362노트

반응식

HRID 1009362 반응식
O.[Na].[F:3][C:4]1[CH:31]=[CH:30][C:7]([CH2:8][C:9]2[NH:13][C:12](/[CH:14]=[CH:15]/[C:16]3[CH:21]=[CH:20][C:19]([N:22]4[CH:26]=[C:25]([CH3:27])[N:24]=[CH:23]4)=[C:18]([O:28][CH3:29])[CH:17]=3)=[N:11][N:10]=2)=[CH:6][CH:5]=1.IC.O.[C:35](=O)(O)[O-].[Na+]>C1COCC1.C(OCC)(=O)C>[F:3][C:4]1[CH:5]=[CH:6][C:7]([CH2:8][C:9]2[N:10]([CH3:35])[N:11]=[C:12](/[CH:14]=[CH:15]/[C:16]3[CH:21]=[CH:20][C:19]([N:22]4[CH:26]=[C:25]([CH3:27])[N:24]=[CH:23]4)=[C:18]([O:28][CH3:29])[CH:17]=3)[N:13]=2)=[CH:30][CH:31]=1.[F:3][C:4]1[CH:5]=[CH:6][C:7]([CH2:8][C:9]2[N:13]=[C:12](/[CH:14]=[CH:15]/[C:16]3[CH:21]=[CH:20][C:19]([N:22]4[CH:26]=[C:25]([CH3:27])[N:24]=[CH:23]4)=[C:18]([O:28][CH3:29])[CH:17]=3)[N:11]([CH3:35])[N:10]=2)=[CH:30][CH:31]=1

참가 물질

8

반응물 4

HCID 6328Methyl iodideHCID 71353970Sodium monohydrateHCID 86585896Sodium bicarbonate waterHCID 178489917HCID 178489917, 화합물

생성물 2

HCID 248526785-(4-fluorobenzyl)-3-{(E)-2-[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl]vinyl}-1-methyl-1H-[1,2,4]triazoleHCID 248527803-(4-fluorobenzyl)-5-{(E)-2-[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl]vinyl}-1-methyl-1H-[1,2,4]triazole

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

실험 절차

Sodium hydrate (containing mineral oil at 60%, 6 mg) was added to a solution of 3-(4-fluorobenzyl)-5-{(E)-2-[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl]vinyl}-4H-[1,2,4]triazole (18 mg) in THF (1 mL), and the reaction solution was stirred at room temperature for 30 minutes. Iodomethane (20 mg) was added to the reaction solution, and the reaction solution was then stirred at room temperature for 1.5 hours. Ethyl acetate and saturated sodium bicarbonate water were added to the reaction solution, and the organic layer was separated. The resulting organic layer was dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (elution solvent: ethyl acetate:ethanol=9:1) to obtain 6 mg of 5-(4-fluorobenzyl)-3-{(E)-2-[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl]vinyl}-1-methyl-1H-[1,2,4]triazole and 2 mg of 3-(4-fluorobenzyl)-5-{(E)-2-[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl]vinyl}-1-methyl-1H-[1,2,4]triazole.

후처리

  1. stirringthe reaction solution was then stirred at room temperature for 1.5 hours
  2. customthe organic layer was separated
  3. dry with materialThe resulting organic layer was dried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (elution solvent: ethyl acetate:ethanol=9:1)

출처 및 근거

ORD 기록
ord-0382d362e38145b9bd07403c8e4b99b1
출처 데이터셋
uspto-grants-2011_07
특허 번호
US07973033B2

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