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Sodium hydride → Ethyl 4,5-dibromo-1-(4-fluorobenzyl)-2-({(2-ethoxy-2-oxoethyl)[(4-methylphenyl)sulfonyl]amino}methyl)-1H-pyrrole-3-carboxylate

HRID 2377078
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HRID 2377078 반응식
[Br:1][C:2]1[C:3]([C:18]([O:20][CH2:21][CH3:22])=[O:19])=[C:4]([CH2:16]Br)[N:5]([CH2:8][C:9]2[CH:14]=[CH:13][C:12]([F:15])=[CH:11][CH:10]=2)[C:6]=1[Br:7].[CH3:23][C:24]1[CH:29]=[CH:28][C:27]([S:30]([NH:33][CH2:34][C:35]([O:37][CH2:38][CH3:39])=[O:36])(=[O:32])=[O:31])=[CH:26][CH:25]=1.[H-].[Na+]>C1COCC1>[Br:1][C:2]1[C:3]([C:18]([O:20][CH2:21][CH3:22])=[O:19])=[C:4]([CH2:16][N:33]([CH2:34][C:35]([O:37][CH2:38][CH3:39])=[O:36])[S:30]([C:27]2[CH:26]=[CH:25][C:24]([CH3:23])=[CH:29][CH:28]=2)(=[O:32])=[O:31])[N:5]([CH2:8][C:9]2[CH:14]=[CH:13][C:12]([F:15])=[CH:11][CH:10]=2)[C:6]=1[Br:7]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 24758Sodium hydrideHCID 230685Ethyl 2-(4-methylphenylsulfonamido)acetateHCID 53237464ethyl 4,5-dibromo-2-(bromomethyl)-1-(4-fluorobenzyl)-1H-pyrrole-3-carboxylate

생성물 1

HCID 59855815Ethyl 4,5-dibromo-1-(4-fluorobenzyl)-2-({(2-ethoxy-2-oxoethyl)[(4-methylphenyl)sulfonyl]amino}methyl)-1H-pyrrole-3-carboxylate

시약·촉매·용매 1

HCID 8028
Tetrahydrofuran
용매

실험 절차

To a stirring solution of ethyl 4,5-dibromo-2-(bromomethyl)-1-(4-fluorobenzyl)-1H-pyrrole-3-carboxylate (104.0 g, 0.209 mol) and ethyl N-[(4-methylphenyl)sulfonyl]glycinate (53.7 g, 0.209 mol, prepared by the method of: Ginzel, K. D.; Brungs, P.; Steckhan, E. Tetrahedron 1989, 45, 1691-1701) in anhydrous THF (1.5 L) was added NaH (60% in mineral oil, 8.40 g, 0.210 mol) in several small portions. The mixture was allowed to stir at room temperature for 16 hours. It was quenched with aq. NH4Cl solution, and extracted with ethyl acetate. The organic layer was dried over Na2SO4, concentrated and the residue was purified by column chromatography with ethyl acetate/hexane (1:4, v:v) to provide the title compound as glue-like material (124 g, 88% yield).

후처리

  1. customIt was quenched with aq. NH4Cl solution
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic layer was dried over Na2SO4
  4. concentrationconcentrated
  5. customthe residue was purified by column chromatography with ethyl acetate/hexane (1:4, v:v)

출처 및 근거

ORD 기록
ord-72c4d6ad0da1462aaeb3b583a557d4fc
출처 데이터셋
uspto-grants-2008_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07468375B2

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