Sodium hydride → HCID 66850506, compound

HRID 1948796Notes

Reaction equation

HRID 1948796 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:5]2.[H-].[Na+].[F:18][C:19]1[CH:20]=[C:21]([CH:24]=[CH:25][CH:26]=1)[CH2:22]Br>CN(C=O)C.O.CCOCC>[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH2:22][C:21]1[CH:24]=[CH:25][CH:26]=[C:19]([F:18])[CH:20]=1)[C:6]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:5]2

Participants

7

Reactant 3

HCID 24758Sodium hydrideHCID 680073-Fluorobenzyl bromideHCID 259091Ethyl 5-Bromoindole-2-carboxylate

Product 1

HCID 66850506HCID 66850506, compoundYield 556.7%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent2×

Procedure

A solution of 5.0 g (18.65 mmol) of ethyl 5-bromo-1H-indole-2-carboxylate in 25 ml of dry DMF is added dropwise, at 0° C., to a suspension of 0.96 g (24.24 mmol) of sodium hydride (60%) in 15 ml of dry DMF, maintained under an inert atmosphere. The reaction mixture is stirred at ambient temperature for 1 hour. 4.23 g (2.75 mmol) of 3-fluorobenzyl bromide are subsequently added dropwise, at 0° C. The reaction mixture is then stirred for 18 h at ambient temperature and then diluted with 200 ml of a mixture of water and ethyl acetate (1/1). The resulting mixture is separated by settling out and the aqueous phase is extracted with 2×30 ml of ethyl acetate. The combined organic phases are washed three times with water, dried over sodium sulphate, filtered and concentrated under reduced pressure. The resulting oil is purified by silica gel column chromatography, elution being carried out with a mixture of heptane and ethyl acetate. 5.76 g of the expected product are isolated.

Workup

  1. temperaturemaintained under an inert atmosphere
  2. stirringThe reaction mixture is then stirred for 18 h at ambient temperature
  3. customThe resulting mixture is separated
  4. extractionthe aqueous phase is extracted with 2×30 ml of ethyl acetate
  5. washThe combined organic phases are washed three times with water
  6. dry with materialdried over sodium sulphate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe resulting oil is purified by silica gel column chromatography, elution
  10. additionbeing carried out with a mixture of heptane and ethyl acetate

Sources & evidence

ORD record
ord-c4d2e88f237d4e30958cd6c1c48cb520
Source dataset
uspto-grants-2013_03
Patent number
US08399491B2

Reaction notes

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