Tributylvinyltin → 3-Methyl-1-(phenylsulfonyl)-4-vinyl-1H-indole

HRID 1159779Notes

Reaction equation

HRID 1159779 reaction equation
[CH2:1]([Sn](CCCC)(CCCC)C=C)[CH2:2]CC.Br[C:17]1[CH:25]=[CH:24][CH:23]=[C:22]2[C:18]=1[C:19]([CH3:35])=[CH:20][N:21]2[S:26]([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)(=[O:28])=[O:27]>CC#N>[CH3:35][C:19]1[C:18]2[C:22](=[CH:23][CH:24]=[CH:25][C:17]=2[CH:1]=[CH2:2])[N:21]([S:26]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)(=[O:28])=[O:27])[CH:20]=1

Participants

4

Reactant 2

HCID 81998TributylvinyltinHCID 68716389HCID 68716389, compound3×

Product 1

HCID 687178803-Methyl-1-(phenylsulfonyl)-4-vinyl-1H-indoleYield 204.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Tributyl(vinyl)stannane (0.400 mL, 1.37 mmol) and Pd(PPh3)2OAc2 (51 mg, 0.069 mmol) were added to 4-bromo-3-methyl-1-(phenylsulfonyl)-1H-indole (240 mg, 0.69 mmol; Intermediate 29) in dry MeCN (4 mL). The reaction mixture was irradiated with micro-waves at 180° C. for 720 s. The mixture was combined with earlier batches of this intermediate (followed this experimental and starting with 4-bromo-3-methyl-1-(phenylsulfonyl)-1H-indole, 50 and 310 mg; Intermediate 29), filtered and concentrated. Purification was performed by flash chromatography (30% hexane in DCM). This afforded the product (420 mg, 82%) as a white solid. MS (ESI+) for C17H15NO2S m/z 298 (M+H)+.

Workup

  1. customThe reaction mixture was irradiated with micro-waves at 180° C. for 720 s
  2. filtrationIntermediate 29), filtered
  3. concentrationconcentrated
  4. customPurification

Sources & evidence

ORD record
ord-962a223cb164456ba8ca07be1a8ff846
Source dataset
uspto-grants-2010_10
Patent number
US07812017B2

Reaction notes

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