Sodium hydride → 1-(4-Fluorobenzyl)-5-methanesulfonyl-2-([1,3,4]oxadiazol-2-yl)indole

HRID 1814058Notes

Reaction equation

HRID 1814058 reaction equation
[CH3:1][S:2]([C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[NH:10][C:9]([C:14]1[O:15][CH:16]=[N:17][N:18]=1)=[CH:8]2)(=[O:4])=[O:3].[H-].[Na+].[F:21][C:22]1[CH:29]=[CH:28][C:25]([CH2:26]Br)=[CH:24][CH:23]=1>CN(C)C=O>[F:21][C:22]1[CH:29]=[CH:28][C:25]([CH2:26][N:10]2[C:11]3[C:7](=[CH:6][C:5]([S:2]([CH3:1])(=[O:3])=[O:4])=[CH:13][CH:12]=3)[CH:8]=[C:9]2[C:14]2[O:15][CH:16]=[N:17][N:18]=2)=[CH:24][CH:23]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 680214-Fluorobenzyl bromideHCID 1357190635-methansulfonyl-2-([1,3,4]oxadiazol-2-yl)-1H-indole

Product 1

HCID 154868601-(4-Fluorobenzyl)-5-methanesulfonyl-2-([1,3,4]oxadiazol-2-yl)indole

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of the crude product (200 mg) of 5-methansulfonyl-2-([1,3,4]oxadiazol-2-yl)-1H-indole in N,N-dimethylformamide (8 ml), 60% sodium hydride (40 mg) was added at 0° C. under nitrogen atmosphere and the mixture was stirred for 5 minutes, followed by addition of 4-fluorobenzyl bromide (215 mg), and the mixture was stirred for 3 hours. To the reaction solution was then added water and the mixture was extracted with ethyl acetate. The organic layer was washed with a saturated aqueous NaCl solution, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The resulting residue was separated using silica gel column chromatography (hexane:ethyl acetate=1:2) to obtain 67 mg of the desired product as a white powder.

Workup

  1. stirringthe mixture was stirred for 3 hours
  2. extractionadded water and the mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with a saturated aqueous NaCl solution
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe resulting residue was separated

Sources & evidence

ORD record
ord-d0b08b52f7bc4281af385519f74752c6
Source dataset
uspto-grants-2005_04
Patent number
US06875770B2

Reaction notes

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