N,N-Dimethylpropargylamine → HCID 58476641, compound

HRID 1672241Notes

Reaction equation

HRID 1672241 reaction equation
Br[C:2]1[C:3]([CH3:10])=[N:4][C:5]([CH3:9])=[C:6]([Br:8])[CH:7]=1.[CH2:11]([N:14]([CH3:16])[CH3:15])[C:12]#[CH:13]>C(NCC)C.CCOC(C)=O.C([O-])([O-])=O.[Na+].[Na+].[Cu](I)I.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>[Br:8][C:6]1[CH:7]=[C:2]([C:13]#[C:12][CH2:11][N:14]([CH3:16])[CH3:15])[C:3]([CH3:10])=[N:4][C:5]=1[CH3:9]

Participants

8

Reactant 2

HCID 81643N,N-DimethylpropargylamineHCID 8172173,5-dibromo-2,6-dimethylpyridine

Product 1

HCID 58476641HCID 58476641, compoundYield 51%

Reagents, catalysts & solvents 5

HCID 83717Copper iodideCatalystHCID 6102075Dichlorobis(triphenylphosphine)palladiumCatalystHCID 8021DiethylamineSolventHCID 8857Ethyl AcetateSolventHCID 10340Sodium CarbonateSolvent

Conditions

Temperature
50 °C

Procedure

To a mixture of 3,5-dibromo-2,6-dimethylpyridine (605 mg, 2.54 mmol), copper iodide (22 mg, 0.11 mmol) and bis(triphenylphosphine)palladium(II)chloride (41 mg, 0.058 mmol) in diethylamine (3.0 mL) was added propargyl(dimethylamine) (0.27 mL, 2.50 mmol). The reaction mixture was allowed to stir for 15 h at 50° C. and was then allowed to cool to rt. The resulting mixture was diluted with EtOAc (30 mL) and 1M aqueous Na2CO3 (20 mL). After stirring for 30 min, the organic solution was separated and the aqueous solution was extracted with EtOAc (2×15 mL). The organic solutions were combined, washed with water and brine, dried over Na2SO4, filtered and concentrated. The residue was purified by column chromatography to give 3-(5-bromo-2,6-dimethylpyridin-3-yl)-N,N-dimethylprop-2-yn-1-amine (313 mg, 51%) as a dark oil. LCMS (AA): Rt=1.47 min, m/z=267.1 (M−H), 269.1 (M+H).

Workup

  1. temperatureto cool to rt
  2. stirringAfter stirring for 30 min
  3. customthe organic solution was separated
  4. extractionthe aqueous solution was extracted with EtOAc (2×15 mL)
  5. washwashed with water and brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-3bc81239678f4ec1bb1fd514bea6c1b1
Source dataset
uspto-grants-2011_08
Patent number
US07998952B2

Reaction notes

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