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Sodium hydride → 4-(4-Bromo-2-fluorobenzyl)-5-n-butyl-2-[2-chloro-5-(methoxycarbonyl)phenyl]-2,4-dihydro-3H-1,2,4-triazol-3-one

HRID 36284
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HRID 36284 반응식
[CH2:1]([C:5]1[NH:6][C:7](=[O:21])[N:8]([C:10]2[CH:15]=[C:14]([C:16]([O:18][CH3:19])=[O:17])[CH:13]=[CH:12][C:11]=2[Cl:20])[N:9]=1)[CH2:2][CH2:3][CH3:4].[H-].[Na+].[H][H].[Br:26][C:27]1[CH:34]=[CH:33][C:30]([CH2:31]Br)=[C:29]([F:35])[CH:28]=1>CN(C=O)C.O>[Br:26][C:27]1[CH:34]=[CH:33][C:30]([CH2:31][N:6]2[C:5]([CH2:1][CH2:2][CH2:3][CH3:4])=[N:9][N:8]([C:10]3[CH:15]=[C:14]([C:16]([O:18][CH3:19])=[O:17])[CH:13]=[CH:12][C:11]=3[Cl:20])[C:7]2=[O:21])=[C:29]([F:35])[CH:28]=1
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참가 물질

7

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HCID 24758Sodium hydrideHCID 27336604-Bromo-2-fluorobenzyl bromideHCID 1357200825-n-Butyl-2-[2-chloro-5-(methoxycarbonyl)phenyl]-2,4-dihydro-3H-1,2,4-triazol-3-oneHCID 178418361HCID 178418361, 화합물

생성물 1

HCID 100060494-(4-Bromo-2-fluorobenzyl)-5-n-butyl-2-[2-chloro-5-(methoxycarbonyl)phenyl]-2,4-dihydro-3H-1,2,4-triazol-3-one수율 40%

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매2회

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온도
50 °C

실험 절차

A mixture of 789 mg (2.55 mmole) of 5-n-butyl-2-[2-chloro-5-(methoxycarbonyl)phenyl]-2,4-dihydro-3H-1,2,4-triazol-3-one (from Step C), 122.4 mg (3.06 mmole) of sodium hydride (60% in oil), and 2 mL of dry DMF was stirred at 50° C. for 2.5 hours, during which time hydrogen was evolved. A solution of 820 mg (3.06 mmole) of 4-bromo-2-fluorobenzyl bromide in DMF was added, and the mixture was stirred at 50° C. overnight. The cooled reaction mixture was diluted with H2O and extracted twice with ethyl acetate. The combined organic phase was washed with H2O and brine and then dried over Na2SO4. The filtered solution was concentrated, and the residue was flash chromatographed on 250 cc of silica gel packed in hexane (gradient elution with 6:1 to 5:1 hexane-EtOAc; some unreacted starting material was recovered by further elution with 95:5 CH2Cl2 --MeOH), yielding 503 mg (40%) of the title compound as an orange gum (TLC in 4:1 hexane-EtOAc), mass spectrum (FAB) m/e 496, 498 (M+1)+ .

후처리

  1. customThe cooled reaction mixture
  2. extractionextracted twice with ethyl acetate
  3. washThe combined organic phase was washed with H2O and brine
  4. dry with materialdried over Na2SO4
  5. concentrationThe filtered solution was concentrated
  6. customchromatographed on 250 cc of silica gel
  7. washgradient elution with 6:1 to 5:1 hexane-EtOAc
  8. customwas recovered by further elution with 95:5 CH2Cl2

출처 및 근거

ORD 기록
ord-bea94300c7df438382147d599c77b1a9
출처 데이터셋
uspto-grants-1995_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05411980

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