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Triethylamine → Dimethyl-(2-pyridin-4-ylethynyl-pyridin-3-yl)-amine

HRID 659938
Notes
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Reaction equation

HRID 659938 reaction equation
Br[C:2]1[C:7]([N:8]([CH3:10])[CH3:9])=[CH:6][CH:5]=[CH:4][N:3]=1.[C:11]([C:13]1[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=1)#[CH:12].C(N(CC)CC)C.[Cl-].[NH4+]>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.CN(C)C=O>[CH3:9][N:8]([CH3:10])[C:7]1[C:2]([C:12]#[C:11][C:13]2[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=2)=[N:3][CH:4]=[CH:5][CH:6]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 25517Ammonium ChlorideHCID 6428014-EthynylpyridineHCID 866434982-bromo-N,N-dimethylpyridin-3-amine

Product 1

HCID 68429284Dimethyl-(2-pyridin-4-ylethynyl-pyridin-3-yl)-amineYield 45%

Reagents, catalysts & solvents 3

HCID 83717
Copper iodide
Catalyst
HCID 178418476HCID 178418476, compoundCatalyst
HCID 6228DimethylformamideSolvent

Procedure

A mixture of 2 g of (2-Bromo-pyridin-3-yl)-dimethyl-amine (9.95 mmoles), 1.24 g of 4-ethynyl pyridine (12 mmoles) in 120 mL of a 1/1 mixture of triethylamine and dimethylformamide is stirred under argon at room temperature. 750 mg of bis(triphenylphosphine)palladium dichloride and 400 mg of copper iodide are added to the reaction mixture which is further stirred at room temperature for 3 hours. The reaction mixture is poured into ammonium chloride solution and extracted with ethyl acetate. The organic phase is washed with water and dried over magnesium sulfate. The solid residue after concentration is purified by chromatography on silica gel (ethylacetate/hexane 1/1) to give 1 g of Dimethyl-(2-pyridin-4-ylethynyl-pyridin-3-yl)-amine as orange oil.

Workup

  1. stirringis further stirred at room temperature for 3 hours
  2. extractionextracted with ethyl acetate
  3. washThe organic phase is washed with water
  4. dry with materialdried over magnesium sulfate
  5. concentrationThe solid residue after concentration
  6. customis purified by chromatography on silica gel (ethylacetate/hexane 1/1)

Sources & evidence

ORD record
ord-4951c305bfd4457389ec8e82d453e684
Source dataset
uspto-grants-2011_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08084395B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes