2-Methoxypropene → 1-benzenesulfonyl-6-bromo-5-(1-methoxy-1-methyl-ethoxymethyl)-1H-indole

HRID 221928Notes

Reaction equation

HRID 221928 reaction equation
[C:1]1([S:7]([N:10]2[C:18]3[C:13](=[CH:14][C:15]([CH2:20][OH:21])=[C:16]([Br:19])[CH:17]=3)[CH:12]=[CH:11]2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:22][O:23][C:24]([CH3:26])=[CH2:25].C(=O)([O-])[O-].[K+].[K+]>C1COCC1.C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1>[C:1]1([S:7]([N:10]2[C:18]3[C:13](=[CH:14][C:15]([CH2:20][O:21][C:24]([O:23][CH3:22])([CH3:26])[CH3:25])=[C:16]([Br:19])[CH:17]=3)[CH:12]=[CH:11]2)(=[O:8])=[O:9])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 3

HCID 83002-MethoxypropeneHCID 11430Potassium CarbonateHCID 59488751(1-benzenesulfonyl-6-bromo-1H-indol-5-yl)methanol

Product 1

HCID 594887731-benzenesulfonyl-6-bromo-5-(1-methoxy-1-methyl-ethoxymethyl)-1H-indoleYield 99%

Reagents, catalysts & solvents 2

HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)CatalystHCID 8028TetrahydrofuranSolvent

Procedure

Under a nitrogen stream, to a solution of (1-benzenesulfonyl-6-bromo-1H-indol-5-yl)methanol (234 mg, 0.64 mmol) and pyridinium p-toluenesulfonate (4 mg, 0.02 mmol) in THF (0.7 mL) was added 2-methoxypropene (92 μL, 0.96 mmol) under ice cooling, and the resultant mixture was stirred at the same temperature for 1 hour. To the reaction mixture was added saturated aqueous potassium carbonate. The resultant mixture was then twice extracted with ethyl acetate. The organic layer was dried (anhydrous magnesium sulfate). Solvent was then removed by distillation under reduced pressure, to thereby obtain the titled compound (277 mg, 99%).

Workup

  1. extractionThe resultant mixture was then twice extracted with ethyl acetate
  2. dry with materialThe organic layer was dried (anhydrous magnesium sulfate)
  3. customSolvent was then removed by distillation under reduced pressure

Sources & evidence

ORD record
ord-69233a70e87042f2acccedfeca2e8042
Source dataset
uspto-grants-2012_06
Patent number
US08207134B2

Reaction notes

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