Stannane, tributyl-1-cyclopenten-1-yl- → HCID 67273154、化合物

HRID 1020917ノート

反応式

HRID 1020917 の反応式
[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

参加物

5

反応物 2

HCID 10915290Stannane, tributyl-1-cyclopenten-1-yl-HCID 67274065HCID 67274065、化合物

生成物 1

HCID 67273154HCID 67273154、化合物収率 65%

試薬・触媒・溶媒 2

HCID 178418476HCID 178418476、化合物触媒HCID 6228Dimethylformamide溶媒

反応条件

温度
90 °C

実験手順

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%).

後処理

  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)

出典と根拠

ORDレコード
ord-36f3aa065efc46ad8123bbdb4e93d65c
出典データセット
uspto-grants-2014_05
特許番号
US08716493B2

反応ノート

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