Indole → 1-(3-Bromo-4-methoxy-benzyl)-1H-indole

HRID 1632056Notes

Reaction equation

HRID 1632056 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.[H-].[Na+].[Br:12][C:13]1[CH:18]=[C:17]([CH2:19]Br)[CH:16]=[CH:15][C:14]=1[O:21][CH3:22].[Cl-].[NH4+]>CN(C=O)C.ClCCl>[Br:12][C:13]1[CH:18]=[C:17]([CH:16]=[CH:15][C:14]=1[O:21][CH3:22])[CH2:19][N:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1

Participants

7

Reactant 4

HCID 798IndoleHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 112774622-Bromo-4-(bromomethyl)-1-methoxybenzene

Product 1

HCID 552393951-(3-Bromo-4-methoxy-benzyl)-1H-indoleYield 87%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of indole (250 mg, 2.14 mmol) in DMF (15 mL) was cooled in an ice bath. To this solution was added sodium hydride (64.3 mg, 2.68 mmol), followed by 2-Bromo-4-bromomethyl-1-methoxy-benzene (500 mg, 1.79 mmol). The reaction was warmed to room temperature and stirred overnight. To the reaction was added saturated aqueous ammonium chloride (75 mL) and the layers separated. The organic extract was washed with saturated aqueous ammonium chloride (2×75 mL), water (3×75 mL) and brine (50 mL). The extract was dried over sodium sulfate, and the solvent removed under reduced pressure. To residue was purified by flash silica gel column chromatography eluting with 1:3 hexanes: dichloromethane to give the title compound (I-107, X═CH) (490 mg, 87% yield) which was taken into further reactions.

Workup

  1. customthe layers separated
  2. extractionThe organic extract
  3. washwas washed with saturated aqueous ammonium chloride (2×75 mL), water (3×75 mL) and brine (50 mL)
  4. dry with materialThe extract was dried over sodium sulfate
  5. customthe solvent removed under reduced pressure
  6. customTo residue was purified by flash silica gel column chromatography
  7. washeluting with 1:3 hexanes

Sources & evidence

ORD record
ord-5b76cdd76b6443958353dc4b759f48e4
Source dataset
uspto-grants-2014_07
Patent number
US08791267B2

Reaction notes

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