Stannane, tributyl-1-cyclopenten-1-yl- → HCID 67273154, 화합물

HRID 1020917노트

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HRID 1020917 반응식
[C:1]1([S:7]([N:10]2[C:18]3[C:13](=[C:14]([O:21][CH3:22])[C:15]([O:19][CH3:20])=[CH:16][CH:17]=3)[CH:12]=[C:11]2I)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C([Sn]([C:37]1[CH2:41][CH2:40][CH2:39][CH:38]=1)(CCCC)CCCC)CCC>CN(C=O)C.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[C:1]1([S:7]([N:10]2[C:18]3[C:13](=[C:14]([O:21][CH3:22])[C:15]([O:19][CH3:20])=[CH:16][CH:17]=3)[CH:12]=[C:11]2[C:37]2[CH2:41][CH2:40][CH2:39][CH:38]=2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

참가 물질

5

반응물 2

HCID 10915290Stannane, tributyl-1-cyclopenten-1-yl-HCID 67274065HCID 67274065, 화합물

생성물 1

HCID 67273154HCID 67273154, 화합물수율 65%

시약·촉매·용매 2

HCID 178418476HCID 178418476, 화합물촉매HCID 6228Dimethylformamide용매

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온도
90 °C

실험 절차

To 539 mg (1.22 mmol) the iodo intermediate from step 2 in 5 mL dry DMF was added 43 mg (0.061 mmol, 5 mol %) of PdCl2(PPh3)2, followed by 870 mg (2.44 mmol, 2 eq) tributylstannylcyclopentene. The reaction was heated to 90° C. for 4 h, concentrated, dissolved in EtOAc and filtered through celite. The EtOAc layer was washed with H2O, aqueous NaCl solution, dried (MgSO4), and concentrated. The product was purified by silica gel chromatography (5-15% EtOAc/hexane) to yield 302 mgs of 1-benzenesulfonyl-2-cyclopent-1-enyl-4,5-dimethoxy-1H-indole (65%).

후처리

  1. concentrationconcentrated
  2. dissolutiondissolved in EtOAc
  3. filtrationfiltered through celite
  4. washThe EtOAc layer was washed with H2O, aqueous NaCl solution
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated
  7. customThe product was purified by silica gel chromatography (5-15% EtOAc/hexane)

출처 및 근거

ORD 기록
ord-36f3aa065efc46ad8123bbdb4e93d65c
출처 데이터셋
uspto-grants-2014_05
특허 번호
US08716493B2

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