Cesium carbonate → HCID 58476654, compound

HRID 1892217Notes

Reaction equation

HRID 1892217 reaction equation
Br[C:2]1[CH:3]=[C:4]([NH2:9])[C:5]([F:8])=[N:6][CH:7]=1.[CH3:10][N:11]([CH3:15])[CH2:12][C:13]#[CH:14].C(=O)([O-])[O-].[Cs+].[Cs+].CC(C1C=C(C(C)C)C(C2C=CC=CC=2P(C2CCCCC2)C2CCCCC2)=C(C(C)C)C=1)C>CN(C=O)C.CC#N.CC#N.Cl[Pd]Cl>[CH3:10][N:11]([CH3:15])[CH2:12][C:13]#[C:14][C:2]1[CH:3]=[C:4]([NH2:9])[C:5]([F:8])=[N:6][CH:7]=1

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 81643N,N-DimethylpropargylamineHCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylHCID 177501445-Bromo-2-fluoropyridin-3-amine

Product 1

HCID 58476654HCID 58476654, compoundYield 45.4%

Reagents, catalysts & solvents 2

HCID 6093782Bis(acetonitrile)dichloropalladiumCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 5-bromo-2-fluoropyridin-3-amine (1.00 g, 5.24 mmol), N,N-dimethylprop-2-yn-1-amine (0.68 mL, 6.28 mmol), and cesium carbonate (3.41 g, 10.5 mmol) in DMF (25 mL) was degassed with argon for 15 min. To this slurry were added bis(acetonitrile)palladium(II) chloride (0.068 g, 0.26 mmol) and Xphos (0.324 g, 0.68 mmol). The suspension was allowed to stir at 50° C. for 4 h under an atmosphere of nitrogen and was then concentrated. The residue was purified by column chromatography to give 5-[3-(dimethylamino)prop-1-yn-1-yl]-2-fluoropyridin-3-amine (0.46 g, 45%).

Workup

  1. customwas degassed with argon for 15 min
  2. concentrationwas then concentrated
  3. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-7fdc022e735841c394ba4ffd1ad31d6d
Source dataset
uspto-grants-2013_08
Patent number
US08507667B2

Reaction notes

Loading…