Hydrofluoric Acid → HCID 13560838, compound

HRID 129515Notes

Reaction equation

HRID 129515 reaction equation
[CH3:1][NH:2][S:3]([CH2:6][C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][CH:15]=1)[NH:12][C:11]([Si](C)(C)C)=[CH:10]2)(=[O:5])=[O:4].F>CC#N>[CH3:1][NH:2][S:3]([CH2:6][C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][CH:15]=1)[NH:12][CH:11]=[CH:10]2)(=[O:5])=[O:4]

Participants

4

Reactant 2

HCID 14917Hydrofluoric AcidHCID 23365818HCID 23365818, compound

Product 1

HCID 13560838HCID 13560838, compoundYield 65.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

5-[[(Methylamino)sulfonyl]methyl]-2-(trimethylsilyl)-1H-indole (4) (1.0 g, 0.00356 mol) was dissolved in CH3CN (40 mL). Concentrated hydrofluoric acid (HF, 1 mL) was added and the mixture was stirred at RT for 3 h. The solvent was removed in vacuo and the residue was dissolved in EtOAc. The organic phase was extracted sequentially with saturated aqueous NaHCO3 and brine, dried over MgSO4, filtered and concentrated in vacuo. Silica gel chromatography (10-100% EtOAc gradient in hexane) of the residue gave the product (5) (0.52 g, 65.2%).

Workup

  1. customThe solvent was removed in vacuo
  2. dissolutionthe residue was dissolved in EtOAc
  3. extractionThe organic phase was extracted sequentially with saturated aqueous NaHCO3 and brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-9ce76a694ab3484e89d8b1afc2caefc1
Source dataset
uspto-grants-1995_11
Patent number
US05468768

Reaction notes

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