Ammonium formate → HCID 15337638, compound

HRID 1003571Notes

Reaction equation

HRID 1003571 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][CH:7]=[C:6]2[C:12]1[CH2:13][CH2:14][N:15](CC2C=CC=CC=2)[CH2:16][CH:17]=1)#[N:2].C([O-])=O.[NH4+]>[Pd].CO>[C:1]([C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][CH:7]=[C:6]2[CH:12]1[CH2:13][CH2:14][NH:15][CH2:16][CH2:17]1)#[N:2]

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 18797384HCID 18797384, compound

Product 1

HCID 15337638HCID 15337638, compoundYield 55.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 0.92 gm (2.9 mMol) 5-cyano-3-(1-benzyl-1,2,3,6-tetrahydropyridin-4-yl)-1H-indole, 1.85 gm (29.3 mMol) ammonium formate and 0.26 gm 5% palladium on carbon in 40 mL methanol were stirred at reflux for 45 minutes. The reaction mixture was then filtered through a pad of Celite and the filtrate concentrated under reduced pressure. The residue was subjected to flash silica gel chromatography, eluting with dichloromethane containing 20% methanol and 2% ammonium hydroxide. Fractions shown to contain product were combined and concentrated under reduced pressure to give 0.36 gm (55%) of the title compound.

Workup

  1. temperatureat reflux for 45 minutes
  2. filtrationThe reaction mixture was then filtered through a pad of Celite
  3. concentrationthe filtrate concentrated under reduced pressure
  4. washeluting with dichloromethane containing 20% methanol and 2% ammonium hydroxide
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-ed1cc1c75d184306b9df6f9768b7dfdd
Source dataset
uspto-grants-2000_04
Patent number
US06046215

Reaction notes

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