Dimethylamine → [5-(2,6-diethyl-phenyl)-1H-pyrrolo[2,3-c]pyridin-3-yl]-acetonitrile

HRID 602556Notes

Reaction equation

HRID 602556 reaction equation
[CH2:1]([C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([CH2:9][CH3:10])[C:4]=1[C:11]1[CH:12]=[C:13]2[CH:19]=[CH:18][NH:17][C:14]2=[CH:15][N:16]=1)[CH3:2].[CH2:20]=O.C[NH:23][CH3:24].[C-]#N.[K+]>CCO>[CH2:1]([C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([CH2:9][CH3:10])[C:4]=1[C:11]1[CH:12]=[C:13]2[C:19]([CH2:20][C:24]#[N:23])=[CH:18][NH:17][C:14]2=[CH:15][N:16]=1)[CH3:2]

Participants

6

Reactant 4

HCID 674DimethylamineHCID 712FormaldehydeHCID 9032Potassium CyanideHCID 116732465-(2,6-diethyl-phenyl)-1H-pyrrolo[2,3-c]pyridine

Product 1

HCID 67152507[5-(2,6-diethyl-phenyl)-1H-pyrrolo[2,3-c]pyridin-3-yl]-acetonitrile

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 5-(2,6-Diethyl-phenyl)-1H-pyrrolo[2,3-c]pyridine (1 g, 4.5 mmol), formaldehyde (37% solution in water, 1.4 mL, 18 mmol), dimethylamine (2 M solution in MeOH, 18 mL, 18 mmol) and EtOH (50 mL) is heated to reflux for 2.5 h. All volatiles are removed under reduced pressure. The residue is mixed with toluene, which is subsequently removed under reduced pressure. The residue is dissolved in DMF (15 mL), KCN (2.6 g, 40 mmol) is added and the mixture was refluxed for 2 h. DMF is removed under reduced pressure, and the residue is purified by chromatography on silica gel (EtOAc) to afford [5-(2,6-diethyl-phenyl)-1H-pyrrolo[2,3-c]pyridin-3-yl]-acetonitrile as colorless oil.

Workup

  1. temperatureis heated
  2. temperatureto reflux for 2.5 h
  3. customAll volatiles are removed under reduced pressure
  4. additionThe residue is mixed with toluene, which
  5. customis subsequently removed under reduced pressure
  6. dissolutionThe residue is dissolved in DMF (15 mL)
  7. temperaturethe mixture was refluxed for 2 h
  8. customDMF is removed under reduced pressure
  9. customthe residue is purified by chromatography on silica gel (EtOAc)

Sources & evidence

ORD record
ord-c4d603bf595248bd862dd566397d96e7
Source dataset
uspto-grants-2011_03
Patent number
US07906528B2

Reaction notes

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