N,N-Dimethylpropargylamine → HCID 58476592, compound

HRID 1672228Notes

Reaction equation

HRID 1672228 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]>C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.Cl[Pd]Cl.[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 6102075Dichlorobis(triphenylphosphine)palladiumCatalyst

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-19d80739484b440c9c41b0ae394da836
Source dataset
uspto-grants-2011_08
Patent number
US07998952B2

Reaction notes

Loading…