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Ethyl Acetate → HCID 67260634、化合物

HRID 2359050
ノート
印刷プレビュー

反応式

HRID 2359050 の反応式
[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
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 699934-Methyloxybenzyl chlorideHCID 67260874HCID 67260874、化合物

生成物 2

HCID 67260634HCID 67260634、化合物収率 168.3%HCID 67261945HCID 67261945、化合物収率 80%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-36f3f46a52074ab1b29cba55602ed53e
出典データセット
uspto-grants-2014_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08685974B2

反応ノート

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