Bromide ion → 5-Nitro-N-phenyl-1-(2-phenylethyl)-1H-indole-2-carboxamide

HRID 1824990Notes

Reaction equation

HRID 1824990 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][C:8]([C:13]([NH:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:14])=[CH:7]2)([O-:3])=[O:2].[OH-].[Na+].Br[CH2:25][CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.[H-].[Na+].[Br-].Cl>CN(C)C=O>[N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[N:9]([CH2:25][CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[C:8]([C:13]([NH:15][C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1)=[O:14])=[CH:7]2)([O-:3])=[O:2]

Participants

8

Reactant 6

HCID 259Bromide ionHCID 313Hydrochloric AcidHCID 7666Phenethyl bromideHCID 14798Sodium HydroxideHCID 24758Sodium hydrideHCID 135231415-nitro-N-phenyl-1H-indole-2-carboxamide

Product 1

HCID 221446385-Nitro-N-phenyl-1-(2-phenylethyl)-1H-indole-2-carboxamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Under argon, 200 mg (0.71 mmol) of 5-nitro-N-phenyl-1H-indole-2-carboxamide from Example XLVIII are initially charged in 5 ml of dimethylformamide. 85.3 mg (2.13 mmol) of sodium hydroxide (60% dispersion in paraffin) are added a little at a time, and the mixture is stirred at RT for 30 min. 657 mg (3.56 mmol) of (2-bromoethyl)benzene are then added, and the mixture is stirred at 100° C. for another 5 h. To terminate the reaction, a further 3 eq. of sodium hydride and 5 eq. of bromide are added, and the mixture is stirred at 100° C. for 7 hours. The reaction mixture is poured into aqueous hydrochloric acid and extracted with ethyl acetate. The organic phase is dried over sodium sulphate and the solvent is removed using a rotary evaporator. The resulting crude product is purified by column chromatography (silica gel 60, mobile phase: cyclohexane/ethyl acetate 6:1).

Workup

  1. stirringthe mixture is stirred at 100° C. for another 5 h
  2. customTo terminate
  3. customthe reaction
  4. stirringthe mixture is stirred at 100° C. for 7 hours
  5. extractionextracted with ethyl acetate
  6. dry with materialThe organic phase is dried over sodium sulphate
  7. customthe solvent is removed
  8. customa rotary evaporator
  9. customThe resulting crude product is purified by column chromatography (silica gel 60, mobile phase: cyclohexane/ethyl acetate 6:1)

Sources & evidence

ORD record
ord-73ac93b936634d8ea169b298fd8afc7d
Source dataset
uspto-grants-2006_05
Patent number
US07045544B2

Reaction notes

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