4-Iodo-1-acetyl-7-azaindole → 1-Acetyl-1H-pyrrolo[2,3-b]pyridine-4-carbonitrile

HRID 887646Notes

Reaction equation

HRID 887646 reaction equation
I[C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[N:8]([C:11](=[O:13])[CH3:12])[CH:9]=[CH:10][C:3]=12.[C:14]([Cu])#[N:15]>O1CCOCC1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.[Fe+2]>[C:11]([N:8]1[C:4]2[N:5]=[CH:6][CH:7]=[C:2]([C:14]#[N:15])[C:3]=2[CH:10]=[CH:9]1)(=[O:13])[CH3:12]

Participants

6

Reactant 2

HCID 112661324-Iodo-1-acetyl-7-azaindoleHCID 178418546HCID 178418546, compound

Product 1

HCID 219614211-Acetyl-1H-pyrrolo[2,3-b]pyridine-4-carbonitrile

Reagents, catalysts & solvents 3

HCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)CatalystHCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 312751,4-DioxaneSolvent

Procedure

A mixture of 1-(4-iodo-pyrrolo[2,3-b]pyridin-1-yl)-ethanone (4.30 g, step C), CuCN (6.841 g), Pd2 dba3 (0.729 g), and dppf (1.636 g) in 85 mL of dioxane was heated to reflux for 2 h. Solid was removed by filtration through a pad of Celite®. The filtrate was concentrated to give a yellow solid as crude compound, which was purified by chromatography through silica gel (250 g, 5-30% EtOAc/hexanes, stepwise gradient) to afford 1-acetyl-1H-pyrrolo[2,3-b]pyridine-4-carbonitrile as a white fluffy solid.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 2 h
  3. customSolid was removed by filtration through a pad of Celite®
  4. concentrationThe filtrate was concentrated
  5. customto give a yellow solid as crude compound, which
  6. customwas purified by chromatography through silica gel (250 g, 5-30% EtOAc/hexanes, stepwise gradient)

Sources & evidence

ORD record
ord-a3ceaed192a3491b8af469f255d712c7
Source dataset
uspto-grants-2012_08
Patent number
US08247430B2

Reaction notes

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