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

HRID 1020917Notes

Reaction equation

HRID 1020917 reaction equation
[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

Participants

5

Reactant 2

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

Product 1

HCID 67273154HCID 67273154, compoundYield 65%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

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%).

Workup

  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)

Sources & evidence

ORD record
ord-36f3aa065efc46ad8123bbdb4e93d65c
Source dataset
uspto-grants-2014_05
Patent number
US08716493B2

Reaction notes

Loading…