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

HRID 659938

반응식

HRID 659938 반응식
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

참가 물질

8

반응물 4

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

생성물 1

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

시약·촉매·용매 3

HCID 83717Copper iodide촉매HCID 178418476HCID 178418476, 화합물촉매HCID 6228Dimethylformamide용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-4951c305bfd4457389ec8e82d453e684
출처 데이터셋
uspto-grants-2011_12
특허 번호
US08084395B2

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