Sodium hydride → HCID 21848272, compound

HRID 618754Notes

Reaction equation

HRID 618754 reaction equation
[H-].[Na+].[Cl:3][C:4]1[CH:25]=[C:24]2[O:26][CH2:27][O:28][C:23]2=[CH:22][C:5]=1[CH2:6][N:7]1[C:15]2[C:10](=[CH:11][C:12]([OH:16])=[CH:13][CH:14]=2)[CH:9]=[C:8]1[C:17]([O:19][CH2:20][CH3:21])=[O:18].[F:29][C:30]([F:40])([F:39])[C:31]1[CH:38]=[CH:37][C:34]([CH2:35]Br)=[CH:33][CH:32]=1>CN(C=O)C>[Cl:3][C:4]1[CH:25]=[C:24]2[O:26][CH2:27][O:28][C:23]2=[CH:22][C:5]=1[CH2:6][N:7]1[C:15]2[C:10](=[CH:11][C:12]([O:16][CH2:35][C:34]3[CH:33]=[CH:32][C:31]([C:30]([F:29])([F:39])[F:40])=[CH:38][CH:37]=3)=[CH:13][CH:14]=2)[CH:9]=[C:8]1[C:17]([O:19][CH2:20][CH3:21])=[O:18]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 1230621-(Bromomethyl)-4-(trifluoromethyl)benzeneHCID 15433190HCID 15433190, compound

Product 1

HCID 21848272HCID 21848272, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirring suspension of sodium hydride (0.016 g, (60% in mineral oil), 0.402 mmol) in DMF (2 mL) was added ethyl 1-(2-chloro-4,5-methylenedioxybenzyl)-5-hydroxyindole-2-carboxylate (0.100 g, 0.268 mmol). After 15 minutes, 4-trifluoromethylbenzyl bromide (0.096 g, 0.402 mmol) was added. After 1.5 hours, the mixture was partitioned between water and ethyl acetate. The organic layer was washed with water and saturated brine, dried (MgSO4), filtered and concentrated to a residue that was purified by column chromatography (ethyl acetate/hexane) to give the title compound as a white solid (0.124 g, 87%).

Workup

  1. waitAfter 1.5 hours
  2. customthe mixture was partitioned between water and ethyl acetate
  3. washThe organic layer was washed with water and saturated brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated to a residue that
  7. customwas purified by column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-6d9dc0c34c2c446fa67ebef9a497c0f3
Source dataset
uspto-grants-1999_09
Patent number
US05955492

Reaction notes

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