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Ethyl Acetate → HCID 67260634, 화합물

HRID 2359050
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HRID 2359050 반응식
[Br:1][C:2]1[NH:6][N:5]=[C:4]([C:7]2[S:8][C:9]([Cl:12])=[CH:10][CH:11]=2)[C:3]=1[C:13]1[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=1.[H-].[Na+].[CH3:21][O:22][C:23]1[CH:30]=[CH:29][C:26]([CH2:27]Cl)=[CH:25][CH:24]=1.C(OCC)(=O)C>CN(C)C=O>[Br:1][C:2]1[N:6]([CH2:27][C:26]2[CH:29]=[CH:30][C:23]([O:22][CH3:21])=[CH:24][CH:25]=2)[N:5]=[C:4]([C:7]2[S:8][C:9]([Cl:12])=[CH:10][CH:11]=2)[C:3]=1[C:13]1[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=1.[Br:1][C:2]1[C:3]([C:13]2[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=2)=[C:4]([C:7]2[S:8][C:9]([Cl:12])=[CH:10][CH:11]=2)[N:5]([CH2:27][C:26]2[CH:29]=[CH:30][C:23]([O:22][CH3:21])=[CH:24][CH:25]=2)[N:6]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

HCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 699934-Methyloxybenzyl chlorideHCID 67260874HCID 67260874, 화합물

생성물 2

HCID 67260634HCID 67260634, 화합물수율 168.3%HCID 67261945HCID 67261945, 화합물수율 80%

시약·촉매·용매

1
HCID 6228Dimethylformamide용매

실험 절차

To a solution of 4-[5-bromo-3-(5-chloro-2-thienyl)-1H-pyrazol-4-yl]pyridine (14.7 mmol) in 80 mL of N,N-dimethylformamide was added slowly at 0° C. sodium hydride (16.1 mmol). The mixture was stirred 30 min at room temperature prior to dropwise addition of 4-methoxybenzyl chloride (16.1 mmol). The mixture was then stirred for further 5 hours. The mixture was then poured on water and ethyl acetate was added. The aqueous layer was extracted with ethyl acetate and the combined organic extracts were washed with brine, dried over MgSO4, filtered and concentrated. The residue was purified by chromatography on silica gel (heptane/ethyl acetate 4:1 to 1:1) to afford 5.7 g of 4-[5-bromo-3-(5-chloro-2-thienyl)-1-(4-methoxybenzyl)-1H-pyrazol-4-yl]pyridine and 4-[3-bromo-5-(5-chloro-2-thienyl)-1-(4-methoxybenzyl)-1H-pyrazol-4-yl]pyridine (80% yield) as a mixture 2:1 which was used as such in the following step.

후처리

  1. stirringThe mixture was then stirred for further 5 hours
  2. additionwas added
  3. extractionThe aqueous layer was extracted with ethyl acetate
  4. washthe combined organic extracts were washed with brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by chromatography on silica gel (heptane/ethyl acetate 4:1 to 1:1)

출처 및 근거

ORD 기록
ord-36f3f46a52074ab1b29cba55602ed53e
출처 데이터셋
uspto-grants-2014_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08685974B2

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