Ethyl bromoacetate → ethyl {5-[(2',6'-dimethylbiphenyl-3-yl)methoxy]-1H-indol-1-yl}acetate

HRID 1163321Notes

Reaction equation

HRID 1163321 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1[C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([CH2:15][O:16][C:17]2[CH:18]=[C:19]3[C:23](=[CH:24][CH:25]=2)[NH:22][CH:21]=[CH:20]3)[CH:10]=1.[H-].[Na+].Br[CH2:29][C:30]([O:32][CH2:33][CH3:34])=[O:31]>O1CCCC1.CN(C)C=O.C(OCC)(=O)C>[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1[C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([CH2:15][O:16][C:17]2[CH:18]=[C:19]3[C:23](=[CH:24][CH:25]=2)[N:22]([CH2:29][C:30]([O:32][CH2:33][CH3:34])=[O:31])[CH:21]=[CH:20]3)[CH:10]=1

Participants

7

Reactant 3

HCID 7748Ethyl bromoacetateHCID 24758Sodium hydrideHCID 231117535-[(2',6'-dimethylbiphenyl-3-yl)methoxy]-1H-indole

Product 1

HCID 58755253ethyl {5-[(2',6'-dimethylbiphenyl-3-yl)methoxy]-1H-indol-1-yl}acetateYield 83.4%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

5-[(2′,6′-Dimethylbiphenyl-3-yl)methoxy]-1H-indole (0.95 g, 2.90 mmol) was dissolved in a mixed solvent of tetrahydrofuran (30 mL) and N,N-dimethylformamide (4 mL). The solution was ice-cooled, and sodium hydride (60% in oil, 0.12 g, 3.0 mmol) was added, and the mixture was stirred at the same temperature for 20 min. Then, ethyl bromoacetate (0.36 mL, 3.25 mmol) was added to the solution, and the mixture was allowed to warm to room temperature and stirred for 2 days. The reaction solution was diluted with ethyl acetate, washed successively with aqueous citric acid solution, water and brine, dried over magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:10-1:5) to give the title compound (1.0 g, yield 83%) as a pale-yellow oil.

Workup

  1. temperaturecooled
  2. stirringstirred for 2 days
  3. washwashed successively with aqueous citric acid solution, water and brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:10-1:5)

Sources & evidence

ORD record
ord-bc38aaec5cc44c45bef8f67c5d738985
Source dataset
uspto-grants-2010_10
Patent number
US07820837B2

Reaction notes

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