Acetic Acid → 5-bromo-3-(pyridin-3-ylmethyl)-1H-indole

HRID 355984

Reaction equation

HRID 355984 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH2:7][CH2:8][CH:9]=O)[CH:2]=1.Cl.[Br:12][C:13]1[CH:18]=[CH:17][C:16]([NH:19]N)=[CH:15][CH:14]=1.C(O)(=O)C>C(O)C>[Br:12][C:13]1[CH:14]=[C:15]2[C:16](=[CH:17][CH:18]=1)[NH:19][CH:9]=[C:8]2[CH2:7][C:3]1[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 121574-Bromophenylhydrazine hydrochlorideHCID 111054123-(Pyridin-3-yl)propanal

Product 1

HCID 189408375-bromo-3-(pyridin-3-ylmethyl)-1H-indole

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 3-pyridin-propionaldehyde (1 g; 0.0074 mol) and of 4-bromophenylhydrazin hydrochloride (1.8 g; 0.0074 mol) with acetic acid (4.44 ml) in absolute ethanol (50 ml) was refluxed for 3 hours. The reaction was then quenched with a saturated solution of aqueous sodium carbonate and the product was extracted with ethyl acetate. The organic extract was dried (MGSO4) and evaporated under vacuum. After purification by Flash Chromatography on silica gel using as eluent methylene chloride/methanol (98/2), the desired compound was obtained.

Workup

  1. customThe reaction was then quenched with a saturated solution of aqueous sodium carbonate
  2. extractionthe product was extracted with ethyl acetate
  3. extractionThe organic extract
  4. customwas dried (MGSO4)
  5. customevaporated under vacuum
  6. customAfter purification by Flash Chromatography on silica gel using as eluent methylene chloride/methanol (98/2)

Sources & evidence

ORD record
ord-bfb74f571a174ea787722b430fdb89e4
Source dataset
uspto-grants-1998_11
Patent number
US05834493

Linked notes

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