Hydrofluoric Acid → 3-(3-hydroxypropyl)-2-trimethylsilyl-N-methyl-1H-indole-5-methanesulfonamide

HRID 1463323Notes

Reaction equation

HRID 1463323 reaction equation
[Si]([O:8][CH2:9][CH2:10][CH2:11][C:12]1[C:20]2[C:15](=[CH:16][CH:17]=[C:18]([CH2:21][S:22]([NH:25][CH3:26])(=[O:24])=[O:23])[CH:19]=2)[NH:14][C:13]=1[Si:27]([CH3:30])([CH3:29])[CH3:28])(C(C)(C)C)(C)C.F>N1C=CC=CC=1.C(OCC)(=O)C>[OH:8][CH2:9][CH2:10][CH2:11][C:12]1[C:20]2[C:15](=[CH:16][CH:17]=[C:18]([CH2:21][S:22]([NH:25][CH3:26])(=[O:24])=[O:23])[CH:19]=2)[NH:14][C:13]=1[Si:27]([CH3:30])([CH3:28])[CH3:29]

Participants

5

Reactant 2

HCID 14917Hydrofluoric AcidHCID 19921656HCID 19921656, compound

Product 1

HCID 199216853-(3-hydroxypropyl)-2-trimethylsilyl-N-methyl-1H-indole-5-methanesulfonamideYield 99%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 0.0738 g (0.157 mmol, 1.0 equiv.) of 3-(3-t-butyldimethysilyloxypropyl)-2-trimethylsilyl-N-methyl-1H-indole-5-methanesulfonamide in 2 mL of pyridine at 0° C. was added I mL of 48% aqueous hydrofluoric acid. The solution was stirred for 20 minutes at 0° C. The solution was diluted with 25 mL of ethyl acetate and washed with 10 mL of 10% aqueous sodium carbonate. The organic layer was dried over anhydrous sodium sulfate, filtered and concentrated in vacuo to yield 0.0551 g (99%) of 3-(3-hydroxypropyl)-2-trimethylsilyl-N-methyl-1H-indole-5-methanesulfonamide, homogeneous by 1H NMR and TLC.

Workup

  1. washwashed with 10 mL of 10% aqueous sodium carbonate
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-27190e7dc90d4bb1b36664a0526ab231
Source dataset
uspto-grants-1994_04
Patent number
US05300506

Reaction notes

Loading…