N,N-Dimethylpropargylamine → HCID 58476641, compound

HRID 2388032Notes

Reaction equation

HRID 2388032 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.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>[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 178418476HCID 178418476, compoundCatalystHCID 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-88dc41907abb43a7ade4e8ed3ae229bf
Source dataset
uspto-grants-2012_09
Patent number
US08268992B2

Reaction notes

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