Trifluoroacetic acid → 5-[(Methylsulfonyl)methyl]-1H-indole

HRID 1080692Notes

Reaction equation

HRID 1080692 reaction equation
[CH3:1][S:2]([CH2:5][C:6]1[CH:7]=[C:8]2[C:12](=[CH:13][CH:14]=1)[NH:11][C:10]([Si](C)(C)C)=[CH:9]2)(=[O:4])=[O:3].FC(F)(F)C(O)=O>C(Cl)Cl>[CH3:1][S:2]([CH2:5][C:6]1[CH:7]=[C:8]2[C:12](=[CH:13][CH:14]=1)[NH:11][CH:10]=[CH:9]2)(=[O:4])=[O:3]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 233658125-[(Methylsulfonyl)methyl]-2-(trimethylsilyl)-1H-indole

Product 1

HCID 193717855-[(Methylsulfonyl)methyl]-1H-indoleYield 51%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

5-[(Methylsulfonyl)methyl]-2-(trimethylsilyl)-1H-indole (2) (1.5 g, 0.00534 mol) was dissolved in CH2Cl2 (70 mL). Trifluoroacetic acid (2 mL) was added and the mixture was stirred at RT for 2 h. The solvent was concentrated in vacuo and the residue was dissolved in EtOAc and extracted with sat. NaHCO3 and then with brine. The organic phase was dried over MgSO4, filtered and evaporate in vacuo. Silica gel chromatography (50-100% EtOAc gradient in hexane) of the concentrate gave the product 0.57 g, 51%) as a brown oil.

Workup

  1. concentrationThe solvent was concentrated in vacuo
  2. dissolutionthe residue was dissolved in EtOAc
  3. extractionextracted with sat. NaHCO3
  4. dry with materialThe organic phase was dried over MgSO4
  5. filtrationfiltered
  6. customevaporate in vacuo

Sources & evidence

ORD record
ord-723edcb1fd8b4666b874b1995f7c138c
Source dataset
uspto-grants-1996_12
Patent number
US05583149

Reaction notes

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