Indole → HCID 21260630, compound

HRID 634632Notes

Reaction equation

HRID 634632 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+].Cl.Cl[CH2:14][C:15]1[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=1.C(=O)([O-])O.[Na+]>CN(C)C=O>[N:17]1[CH:18]=[CH:19][CH:20]=[C:15]([CH2:14][N:1]2[C:9]3[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=3)[CH:3]=[CH:2]2)[CH:16]=1

Participants

6

Reactant 4

HCID 798IndoleHCID 233943-(Chloromethyl)pyridine hydrochlorideHCID 24758Sodium hydrideHCID 516892Sodium Bicarbonate

Product 1

HCID 21260630HCID 21260630, compoundYield 100.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

Under argon, a dimethylformamide (50 ml) solution of indole (18 g) was added into dimethylformamide (350 ml) in which 60% sodium hydride (7.9 g) was suspended, and the mixture was stirred at room temperature for 30 minutes. A dimethylformamide (100 ml) solution of 3-chloromethylpyridine hydrochloride (25 g) was added at 0° C. and the mixture stirred at room temperature for 18 hours. After the reaction, a saturated aqueous sodium hydrogencarbonate solution was added at 0° C. and the mixture was extracted with ethyl acetate. The organic phase was washed with brine and dried over magnesium sulfate, then the solvent was evaporated in vacuo and the residue was purified by silica gel column chromatography to obtain 1-(3-pyridylmethyl)indole (31.9 g).

Workup

  1. stirringthe mixture stirred at room temperature for 18 hours
  2. customAfter the reaction
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe organic phase was washed with brine
  5. dry with materialdried over magnesium sulfate
  6. customthe solvent was evaporated in vacuo
  7. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-3240b201c77b43e6a4793ffcf5caebec
Source dataset
uspto-grants-2001_02
Patent number
US06184238B2

Reaction notes

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