Potassium Hydroxide → HCID 68558433, compound

HRID 2381933Notes

Reaction equation

HRID 2381933 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7](S(C1C=CC(C)=CC=1)(=O)=O)[CH:6]=[C:5]2[S:21]([N:24]1[CH2:29][CH2:28][O:27][CH2:26][CH2:25]1)(=[O:23])=[O:22].[OH-].[K+]>CO>[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[C:5]2[S:21]([N:24]1[CH2:25][CH2:26][O:27][CH2:28][CH2:29]1)(=[O:22])=[O:23]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 68556481HCID 68556481, compound

Product 1

HCID 68558433HCID 68558433, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 5-fluoro-3-(morpholine-4-sulfonyl)-1-(toluene-4-sulfonyl)-1H-indole (1.3 g) in MeOH (50 mL)/5 N KOH (3 mL) is heated to reflux for 1 h. The reaction mixture is concentrated in vacuo. The residue is diluted with water (30 mL) and acidified with 10 N aqueous HCl to pH 4. The mixture is extracted with EtOAc. The organic layer washed with water, brine and dried (MgSO4), filtered and concentrated in vacuo to afford 5-fluoro-3-(morpholine-4-sulfonyl)-1H-indole (0.8 g, 95%) as a solid. MS: 285 (M+H).

Workup

  1. temperatureto reflux for 1 h
  2. concentrationThe reaction mixture is concentrated in vacuo
  3. additionThe residue is diluted with water (30 mL)
  4. extractionThe mixture is extracted with EtOAc
  5. washThe organic layer washed with water, brine
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-cbe03d8504fc429daf7bfae9cc60f220
Source dataset
uspto-grants-2012_09
Patent number
US08258130B2

Reaction notes

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