Phenethyl bromide → HCID 82087709, compound

HRID 2360120Notes

Reaction equation

HRID 2360120 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][CH2:7][CH2:6]2.[H-].[Na+].Br[CH2:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>CN(C)C=O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[N:8]([CH2:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[CH:7]=[CH:6]2

Participants

5

Reactant 3

HCID 7666Phenethyl bromideHCID 24758Sodium hydrideHCID 107019745-methoxy-2,3-dihydro-1H-indole

Product 1

HCID 82087709HCID 82087709, compoundYield 32.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 5-methoxyindoline (175 mg, 1.17 mmol) in 3.6 mL of dry N,N-dimethylformamide was added sodium hydride (55%, 70 mg, 1.6 mmol) at 0° C. After the reaction mixture was stirred at the same temperature for 30 min, (2-bromoethyl)benzene (0.22 mL, 1.6 mmol) was added with additional stirring at room temperature overnight. After the reaction mixture was quenched with water at 0° C., the solution was extracted with diethyl ether (20 mL) twice. The combined extracts were washed with brine, and dried over MgSO4. After filtration, the filtrate was concentrated in vacuo, and the residue was purified by silica gel column chromatography (hexane/ethyl acetate=95/5 to 85/15) to obtain 5-methoxy-1-phenethylindole (95 mg, 32%).

Workup

  1. stirringwith additional stirring at room temperature overnight
  2. customAfter the reaction mixture was quenched with water at 0° C.
  3. extractionthe solution was extracted with diethyl ether (20 mL) twice
  4. washThe combined extracts were washed with brine
  5. dry with materialdried over MgSO4
  6. filtrationAfter filtration
  7. concentrationthe filtrate was concentrated in vacuo
  8. customthe residue was purified by silica gel column chromatography (hexane/ethyl acetate=95/5 to 85/15)

Sources & evidence

ORD record
ord-58e7b18bae4b42988b2eb0abb9079c53
Source dataset
uspto-grants-2014_04
Patent number
US08686024B2

Reaction notes

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