Sodium hydride → HCID 18435814, compound

HRID 2304761Notes

Reaction equation

HRID 2304761 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])=[C:5]2[O:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.[F:24][C:25]1[CH:32]=[CH:31][C:28]([CH2:29]Br)=[CH:27][CH:26]=1.[H-].[Na+]>CN(C=O)C>[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH2:29][C:28]1[CH:31]=[CH:32][C:25]([F:24])=[CH:26][CH:27]=1)[C:6]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[C:5]2[O:16][CH2:17][C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 680214-Fluorobenzyl bromideHCID 18435807HCID 18435807, compound

Product 1

HCID 18435814HCID 18435814, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of 5.57 g of ethyl 5-bromo-3-(phenylmethoxy)indole-2-carboxylate and 2.9 mL of 4-fluorobenzyl bromide in 40 mL of DMF at 0° C. was added 887 mg of a NaH suspension (60% in oil) and the resulting reaction mixture was warmed slowly to room temperature with continuous stirring. After 0.5 hour, the reaction was quenched with saturated aqueous NH4Cl and extracted twice with ethyl acetate/ether 1:1. The organic phase was washed with water (4×), brine and dried over anhydrous Na2SO4. Flash chromatography (toluene) and recrystallization from hexane yielded 5.99 g of the title compound as a white solid.

Workup

  1. customthe resulting reaction mixture
  2. customthe reaction was quenched with saturated aqueous NH4Cl
  3. extractionextracted twice with ethyl acetate/ether 1:1
  4. washThe organic phase was washed with water (4×), brine
  5. dry with materialdried over anhydrous Na2SO4
  6. customFlash chromatography (toluene) and recrystallization from hexane

Sources & evidence

ORD record
ord-dad6ed8e54a04904909a2abe52f0f74e
Source dataset
uspto-grants-2002_08
Patent number
US06436965B1

Reaction notes

Loading…