Stannane, tributyl-1-cyclopenten-1-yl- → HCID 67273815, compound

HRID 1020908Notes

Reaction equation

HRID 1020908 reaction equation
[C:1]1([S:7]([N:10]2[C:14]3=[N:15][CH:16]=[CH:17][C:18]([O:19][CH3:20])=[C:13]3[CH:12]=[C:11]2I)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C([Sn](CCCC)(CCCC)[C:27]1[CH2:31][CH2:30][CH2:29][CH:28]=1)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:14]3[C:13](=[C:18]([O:19][CH3:20])[CH:17]=[CH:16][N:15]=3)[CH:12]=[C:11]2[C:27]2[CH2:31][CH2:30][CH2:29][CH:28]=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 672735222-Iodo-4-methoxy-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 67273815HCID 67273815, compoundYield 64.9%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 1-benzenesulfonyl-2-iodo-4-methoxy-1H-pyrrolo[2,3-b]pyridine (1.1 g, 2.65 mmol), tributyl-cyclopent-1-enyl-stannane (1.9 g, 5.31 mmol), and bis(triphenylphosphine)palladium(II) chloride (93 mg) in DMF (10 mL) was heated in a sealed tube to 90° C. for seven hours. The mixture was washed with hexanes (2×10 mL) and the DMF phase was concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel (gradient elution of 10-35% EtOAc/hexanes) to give 0.61 g of 1-benzenesulfonyl-2-cyclopent-1-enyl-4-methoxy-7-azaindole as a yellow solid; MS (m/z) 355 (M+H).

Workup

  1. washThe mixture was washed with hexanes (2×10 mL)
  2. concentrationthe DMF phase was concentrated under reduced pressure
  3. customThe residue was purified by flash chromatography on silica gel (gradient elution of 10-35% EtOAc/hexanes)

Sources & evidence

ORD record
ord-4ca58ec96a4c4d378a246351cebbd546
Source dataset
uspto-grants-2014_05
Patent number
US08716493B2

Reaction notes

Loading…