1,2-Dimethoxyethane → 5-[(Methylsulfonyl)methyl]-2-(trimethylsilyl)-1H-indole
Reaction equation
COCCOC.I[C:8]1[CH:13]=[C:12]([CH2:14][S:15]([CH3:18])(=[O:17])=[O:16])[CH:11]=[CH:10][C:9]=1[NH2:19].[CH3:20][Si:21]([C:24]#[C:25][Si](C)(C)C)([CH3:23])[CH3:22].C([O-])([O-])=O.[Na+].[Na+]>CCCCCC.CCOC(C)=O.CO>[CH3:18][S:15]([CH2:14][C:12]1[CH:13]=[C:8]2[C:9](=[CH:10][CH:11]=1)[NH:19][C:24]([Si:21]([CH3:23])([CH3:22])[CH3:20])=[CH:25]2)(=[O:17])=[O:16]Participants
8
Reactant 4
Product 1
Reagents, catalysts & solvents 3
Procedure
To a solution of 1,2-dimethoxyethane (DME, 70 mL) was added 2-iodo-4-[(methylsulfonyl)methyl]benzenamine (1) (1.9 g, 0.0061 mol), bis(trimethylsilyl) acetylene (1.56 g, 0.00915 mol), tetrakistriphenylphosphine Pd(O) (0.705 g, 0.00061 mol) and saturated aqueous Na2CO3 (5 mL). The reaction was heated at reflux for 48 h. The solvent was removed in vacuo and the residue was dissolved in EtOAc and washed with brine. The organic layer was dried over MgSO4, filtered and evaporated to give the crude product. Silica gel chromatography (20-100% EtOAc gradient in hexane followed by 5-10% MeOH gradient in EtOAc) of the concentrate afforded the product (2) (1.42 g, 83%) as a brown oil.
Workup
- temperatureThe reaction was heated
- temperatureat reflux for 48 h
- customThe solvent was removed in vacuo
- dissolutionthe residue was dissolved in EtOAc
- washwashed with brine
- dry with materialThe organic layer was dried over MgSO4
- filtrationfiltered
- customevaporated
- customto give the crude product
Sources & evidence
- ORD record
- ord-9904ca5f6c864878a9351cd2c2fc041e
- Source dataset
- uspto-grants-1996_12
- Patent number
- US05583149
Reaction notes
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