Tri(butyl)vinyltin → HCID 68713184, compound

HRID 1159793Notes

Reaction equation

HRID 1159793 reaction equation
Br[C:2]1[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[C:7]2[C:3]=1[CH:4]=[CH:5][N:6]2[S:13]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)(=[O:15])=[O:14].[CH2:22](C([Sn])=C(CCCC)CCCC)[CH2:23]CC>C(#N)C>[CH:22]([C:2]1[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[C:7]2[C:3]=1[CH:4]=[CH:5][N:6]2[S:13]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)(=[O:15])=[O:14])=[CH2:23]

Participants

4

Reactant 2

HCID 53438229Tri(butyl)vinyltinHCID 68715889HCID 68715889, compound2×

Product 1

HCID 68713184HCID 68713184, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

4-Bromo-7-methoxy-1-(phenylsulfonyl)-1H-indole (200 mg, 0.55 mmol, Intermediate 43), tributylvinyltin (348 mg, 1.1 mmol) and bis(acetate)bis(triphenylphosphine)-palladium(II) (46 mg, 0.06 mmol) were mixed in dry acetonitrile (2 mL) and heated in microwave at 180 deg for 10 min. The reaction mixture was filtered through celite and concentrated. The crude product was purified by column chromatography on silica (CHCl3/hexane 7:3) to give 4-vinyl-7-methoxy-1-(phenylsulfonyl)-1H-indole, 0.19 g, which was used immediately in the next step.

Workup

  1. temperatureheated in microwave at 180 deg for 10 min
  2. filtrationThe reaction mixture was filtered through celite
  3. concentrationconcentrated
  4. customThe crude product was purified by column chromatography on silica (CHCl3/hexane 7:3)

Sources & evidence

ORD record
ord-cdd71fbcc42341e4910c99bb231c5aae
Source dataset
uspto-grants-2010_10
Patent number
US07812017B2

Reaction notes

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