N,N-Dimethylpropargylamine → HCID 58476592, compound

HRID 1892218Notes

Reaction equation

HRID 1892218 reaction equation
Br[C:2]1[CH:3]=[C:4]([NH2:8])[CH:5]=[N:6][CH:7]=1.[CH3:9][N:10]([CH3:14])[CH2:11][C:12]#[CH:13]>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Cu](I)I>[CH3:9][N:10]([CH3:14])[CH2:11][C:12]#[C:13][C:2]1[CH:3]=[C:4]([NH2:8])[CH:5]=[N:6][CH:7]=1

Participants

5

Reactant 2

HCID 81643N,N-DimethylpropargylamineHCID 8176813-Amino-5-bromopyridine

Product 1

HCID 58476592HCID 58476592, compoundYield 54.3%

Reagents, catalysts & solvents 2

HCID 83717Copper iodideCatalystHCID 178418476HCID 178418476, compoundCatalyst

Conditions

Temperature
80 °C

Procedure

To a degassed solution of 5-bromopyridin-3-amine (1.00 g, 5.78 mmol) and N,N-dimethylprop-2-yn-1-amine (1.57 mL, 14.6 mmol) in TEA (26 mL) were added bis(triphenylphosphine)palladium(II) chloride (0.203 g, 0.29 mmol) and copper iodide (0.110 g, 0.58 mmol). The reaction mixture was allowed to stir under an atmosphere of argon at 80° C. for 14 h. The reaction mixture was allowed to cool to rt and then filtered through Celite. The filter pad was washed with EtOAc and the filtrate was concentrated. The residue was purified by column chromatography to give 5-[3-(dimethylamino)prop-1-yn-1-yl]pyridin-3-amine (0.55 g, 54%).

Workup

  1. temperatureto cool to rt
  2. filtrationfiltered through Celite
  3. washThe filter pad was washed with EtOAc
  4. concentrationthe filtrate was concentrated
  5. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-8affa53a675d49a2b6554e11d6bd1167
Source dataset
uspto-grants-2013_08
Patent number
US08507667B2

Reaction notes

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