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N-bromobutanimide → methyl 5-bromo-4-(tert-butoxycarbonyl)-6-cyclohexyl-4H-thieno[3,2-b]pyrrole-2-carboxylate

HRID 505808
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HRID 505808 반응식
[C:1]([O:5][C:6]([N:8]1[CH:12]=[C:11]([CH:13]2[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]2)[C:10]2[S:19][C:20]([C:22]([O:24][CH3:25])=[O:23])=[CH:21][C:9]1=2)=[O:7])([CH3:4])([CH3:3])[CH3:2].C1C(=O)N([Br:33])C(=O)C1>C(Cl)Cl>[Br:33][C:12]1[N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[C:9]2[CH:21]=[C:20]([C:22]([O:24][CH3:25])=[O:23])[S:19][C:10]=2[C:11]=1[CH:13]1[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1
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4

반응물 2

HCID 67184N-bromobutanimideHCID 68471407methyl 4-(tert-butoxycarbonyl)-6-cyclohexyl-4H-thieno[3,2-b]pyrrole-2-carboxylate

생성물 1

HCID 67298537methyl 5-bromo-4-(tert-butoxycarbonyl)-6-cyclohexyl-4H-thieno[3,2-b]pyrrole-2-carboxylate수율 98%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

A solution (0.1 M) of methyl 4-(tert-butoxycarbonyl)-6-cyclohexyl-4H-thieno[3,2-b]pyrrole-2-carboxylate in DCM was cooled to 0° C. and treated with NBS (1.1 eq.) then it was left to warm to RT. The reaction was quenched with aqueous Na2S2O3 (saturated solution) and extracted with AcOEt. The organic phase was washed with aqueous Na2S2O3 (saturated solution) and brine then dried and concentrated, affording the title compound (98%) as a solid.

후처리

  1. waitit was left
  2. customThe reaction was quenched with aqueous Na2S2O3 (saturated solution)
  3. extractionextracted with AcOEt
  4. washThe organic phase was washed with aqueous Na2S2O3 (saturated solution) and brine
  5. customthen dried
  6. concentrationconcentrated

출처 및 근거

ORD 기록
ord-7db390e8e54745819e5c6987c0ccb94e
출처 데이터셋
uspto-grants-2010_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07781431B2

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