Phenethyl bromide → HCID 22314288, compound

HRID 966063Notes

Reaction equation

HRID 966063 reaction equation
[C:1]([C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[NH:6][C:5]=1[C:13]1[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][CH:14]=1)(=[O:3])[CH3:2].[CH2:20](Br)[CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.[H-].[Na+]>O1CCCC1>[C:1]([C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[N:6]([CH2:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:5]=1[C:13]1[CH:14]=[CH:15][C:16]([Cl:19])=[CH:17][CH:18]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 7666Phenethyl bromideHCID 24758Sodium hydrideHCID 22314347HCID 22314347, compound

Product 1

HCID 22314288HCID 22314288, compoundYield 46%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 3-acetyl-2-(4-chlorophenyl)indole (53.9 mg, 0.2 mmol) and phenethylbromide (30 μL, 0.22 mmol) in tetrahydrofuran is treated with NaH (60% dispersion in mineral oil, 24 mg, 0.6 mmol) at room temperature, shaken for 6 h, quenched with saturated NaHCO3 and extracted with ethyl acetate. The extracts are combined and concentrated in vacuo to afford the title product, 34 mg (46% yield), identified by NMR and mass spectral analyses.

Workup

  1. customquenched with saturated NaHCO3
  2. extractionextracted with ethyl acetate
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-6a72239c8f2746638c2c60e331cf728e
Source dataset
uspto-grants-2005_10
Patent number
US06951881B2

Reaction notes

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