Water → HCID 66885857, compound

HRID 2353016Notes

Reaction equation

HRID 2353016 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][CH:12]=[C:13]2[C:17]=1[NH:16][CH:15]=[CH:14]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[CH3:20][C:21]1[CH:28]=[CH:27][C:24]([CH2:25]Cl)=[CH:23][CH:22]=1.O>CN(C)C=O>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][CH:12]=[C:13]2[C:17]=1[N:16]([CH2:20][C:21]1[CH:28]=[CH:27][C:24]([CH3:25])=[CH:23][CH:22]=1)[CH:15]=[CH:14]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 77224-Methylbenzyl chlorideHCID 24758Sodium hydrideHCID 2607987-(Benzyloxy)-1H-indole

Product 1

HCID 66885857HCID 66885857, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 7-benzyloxy-1H-indole (0.3 g) in N,N-dimethylformamide (5 mL) was added sodium hydride (55% 70 mg) under ice-cooling, and the mixture was stirred for 10 minutes. To the reaction mixture was added 4-methylbenzyl chloride (0.19 mL), and the mixture was stirred at room temperature for 2 hours. The reaction mixture was poured into water, and the resulting mixture was extracted with diethyl ether. The extract was washed with water and brine, and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure to give 7-benzyloxy-1-(4-methylbenzyl)-1H-indole (0.43 g). This material was dissolved in tetrahydrofuran (6 mL). To the solution was added 10% palladium-carbon powder (50 mg), and the mixture was stirred at room temperature under a hydrogen atmosphere for 5 hours. The insoluble material was removed by filtration, and the filtrate was concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (eluent: n-hexane/ethyl acetate=5/1) to give the title compound (86 mg).

Workup

  1. temperaturecooling
  2. stirringthe mixture was stirred at room temperature for 2 hours
  3. extractionthe resulting mixture was extracted with diethyl ether
  4. washThe extract was washed with water and brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-d72737f6ce8d41fea67ef751598a5bc2
Source dataset
uspto-grants-2010_07
Patent number
US07749972B2

Reaction notes

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