Sodium Hydroxide → HCID 24985148, compound

HRID 503940Notes

Reaction equation

HRID 503940 reaction equation
[OH-].[Na+].C1(S([N:12]2[C:20]3[C:15](=[CH:16][C:17]([F:21])=[CH:18][CH:19]=3)[C:14]([S:22]([C:25]3[CH:30]=[CH:29][C:28]([CH:31]4[CH2:35][CH2:34][N:33]([CH3:36])[CH2:32]4)=[C:27]([CH3:37])[CH:26]=3)(=[O:24])=[O:23])=[CH:13]2)(=O)=O)C=CC=CC=1>CO>[F:21][C:17]1[CH:16]=[C:15]2[C:20](=[CH:19][CH:18]=1)[NH:12][CH:13]=[C:14]2[S:22]([C:25]1[CH:30]=[CH:29][C:28]([CH:31]2[CH2:35][CH2:34][N:33]([CH3:36])[CH2:32]2)=[C:27]([CH3:37])[CH:26]=1)(=[O:23])=[O:24]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 59428333HCID 59428333, compound

Product 1

HCID 24985148HCID 24985148, compoundYield 67.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

An aqueous solution of NaOH (2 M, 0.8 mL) was added to a solution of 1-benzenesulfonyl-5-fluoro-3-[3-methyl-4-(1-methyl-pyrrolidin-3-yl)-benzenesulfonyl]-1H-indole (0.209 g, 0.4045 mmol) in MeOH (1 mL) and the resulting mixture was stirred at room temperature for 5 hours. The solvent was evaporated under reduced pressure and the crude material was purified via flash chromatography (DCM/MeOH/NH4OH) to give 0.102 g of 5-fluoro-3-[3-methyl-4-(1-methyl-pyrrolidin-3-yl)-benzenesulfonyl]-1H-indole as a white foam. MP=86.5-93.5° C.; MS (M+H)=378.

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. customthe crude material was purified via flash chromatography (DCM/MeOH/NH4OH)

Sources & evidence

ORD record
ord-5de00b65d3974c5aaf0b3cac0c9875b5
Source dataset
uspto-grants-2010_08
Patent number
US07776910B2

Reaction notes

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