Sodium hydride → N-(4-Fluoro-benzyl)-4-[3-(3-oxo-cyclopentyl)-indole-1-sulfonyl]-benzamide

HRID 737025Notes

Reaction equation

HRID 737025 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH:10]2[CH2:14][CH2:13][C:12](=[O:15])[CH2:11]2)=[CH:2]1.[H-].[Na+].[F:18][C:19]1[CH:38]=[CH:37][C:22]([CH2:23][NH:24][C:25]([C:27]2[CH:32]=[CH:31][C:30]([S:33](Cl)(=[O:35])=[O:34])=[CH:29][CH:28]=2)=[O:26])=[CH:21][CH:20]=1>CN(C=O)C>[F:18][C:19]1[CH:20]=[CH:21][C:22]([CH2:23][NH:24][C:25](=[O:26])[C:27]2[CH:32]=[CH:31][C:30]([S:33]([N:1]3[C:9]4[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=4)[C:3]([CH:10]4[CH2:14][CH2:13][C:12](=[O:15])[CH2:11]4)=[CH:2]3)(=[O:34])=[O:35])=[CH:29][CH:28]=2)=[CH:37][CH:38]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 113446533-(1H-Indol-3-yl)cyclopentanoneHCID 589751254-(4-Fluoro-benzylcarbamoyl)-benzenesulfonyl chloride

Product 1

HCID 58975183N-(4-Fluoro-benzyl)-4-[3-(3-oxo-cyclopentyl)-indole-1-sulfonyl]-benzamideYield 29.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

Add a 3 nm DMF solution of 3-(1H-Indol-3-yl)-cyclopentanone (500 mg, 2.57 mmol, 1 eq) to a 3 ml DMF solution of NaH (155 mg, 60% by weight, 3.86 mmol, 1.1 eq) under N2 atmosphere. Stir reaction for 15 minutes and then add a 5 ml DMF solution of 4-(4-Fluoro-benzylcarbamoyl)-benzenesulfonyl chloride (1.27 g, 3.86 mmol, 1.1 eq). Stir reaction for 48 hours, remove solvent on rotovap, and purify by silica gel chromatography to give N-(4-Fluoro-benzyl)-4-[3-(3-oxo-cyclopentyl)-indole-1-sulfonyl]-benzamide (375 mg, 22% yield). Mass Spectrum (m/e): 490.53 (MH+).

Workup

  1. customreaction for 15 minutes
  2. stirringStir
  3. customreaction for 48 hours
  4. customremove solvent on rotovap
  5. custompurify by silica gel chromatography

Sources & evidence

ORD record
ord-1231cd481aa8432c979fe53427ab557c
Source dataset
uspto-grants-2009_09
Patent number
US07595339B2

Reaction notes

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