Water → 2-(2-Ethoxycarbonylfuran-5-yl)-1-(4-fluorobenzyl)-5-methanesulfonyl-indole

HRID 1432269Notes

Reaction equation

HRID 1432269 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[O:7][C:8]([C:11]2[NH:12][C:13]3[C:18]([CH:19]=2)=[CH:17][C:16]([S:20]([CH3:23])(=[O:22])=[O:21])=[CH:15][CH:14]=3)=[CH:9][CH:10]=1)=[O:5])[CH3:2].[H-].[Na+].[F:26][C:27]1[CH:34]=[CH:33][C:30]([CH2:31]Br)=[CH:29][CH:28]=1.O>CN(C)C=O>[CH2:1]([O:3][C:4]([C:6]1[O:7][C:8]([C:11]2[N:12]([CH2:31][C:30]3[CH:33]=[CH:34][C:27]([F:26])=[CH:28][CH:29]=3)[C:13]3[C:18]([CH:19]=2)=[CH:17][C:16]([S:20]([CH3:23])(=[O:22])=[O:21])=[CH:15][CH:14]=3)=[CH:9][CH:10]=1)=[O:5])[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 680214-Fluorobenzyl bromideHCID 22504378HCID 22504378, compound

Product 1

HCID 225044342-(2-Ethoxycarbonylfuran-5-yl)-1-(4-fluorobenzyl)-5-methanesulfonyl-indole

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of the compound obtained in Example 29 (3) (0.0457 g) in N,N-dimethylformamide (1.4 ml), 60% sodium hydride (0.006 g) was added at 0° C. under nitrogen atmosphere and the mixture was stirred for 15 minutes, followed by addition of 4-fluorobenzyl bromide (0.02 ml), and the mixture was stirred for 1 hour. The reaction solution was then poured into water and extracted with ethyl acetate. The organic layer was washed with a saturated aqueous NaCl solution, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The resulting residue was separated using silica gel column chromatography (hexane ethyl acetate=1:1) to obtain 0.0403 g of the desired product as a white solid.

Workup

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

Sources & evidence

ORD record
ord-8ad5e5b7a0a64ecd8cd131b47c841eca
Source dataset
uspto-grants-2009_11
Patent number
US07612070B2

Reaction notes

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