Sodium hydride → 2-(2-tetrahydrofuranyl)-5-methanesulfonyl-1-(4-fluorobenzyl)-1H-indole

HRID 1838342Notes

Reaction equation

HRID 1838342 reaction equation
[O:1]1[CH2:5][CH2:4][CH2:3][CH:2]1[C:6]1[NH:7][C:8]2[C:13]([CH:14]=1)=[CH:12][C:11]([S:15]([CH3:18])(=[O:17])=[O:16])=[CH:10][CH:9]=2.[H-].[Na+].[F:21][C:22]1[CH:29]=[CH:28][C:25]([CH2:26]Br)=[CH:24][CH:23]=1.[Cl-].[NH4+]>CN(C)C=O>[O:1]1[CH2:5][CH2:4][CH2:3][CH:2]1[C:6]1[N:7]([CH2:26][C:25]2[CH:28]=[CH:29][C:22]([F:21])=[CH:23][CH:24]=2)[C:8]2[C:13]([CH:14]=1)=[CH:12][C:11]([S:15]([CH3:18])(=[O:17])=[O:16])=[CH:10][CH:9]=2

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 680214-Fluorobenzyl bromideHCID 225044162-(2-tetrahydrofuranyl)-5-methanesulfonyl-1H-indole

Product 1

HCID 98208782-(2-tetrahydrofuranyl)-5-methanesulfonyl-1-(4-fluorobenzyl)-1H-indoleYield 87.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of the compound obtained in Example 13 (2) (113 mg) in N,N-dimethylformamide (5 ml), 60% sodium hydride (25.6 mg) was added under nitrogen atmosphere at 0° C. and the mixture was stirred for 30 minutes, followed by addition of 4-fluorobenzyl bromide (121 mg), and the mixture was stirred for 1 hour. The reaction solution was then poured into a saturated aqueous ammonium chloride solution and extracted with ethyl acetate. The organic layer was washed with water and a saturated aqueous NaCl solution, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The resulting residue was separated using silica gel preparative thin-layer chromatography (hexane:ethyl acetate=1:1) to obtain 139 mg of the desired product as a white powder.

Workup

  1. stirringthe mixture was stirred for 1 hour
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with water
  4. dry with materiala saturated aqueous NaCl solution, dried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe resulting residue was separated

Sources & evidence

ORD record
ord-a671127056ae4e09a5cef723fd514d5c
Source dataset
uspto-grants-2004_01
Patent number
US06673797B1

Reaction notes

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