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

HRID 659938

反応式

HRID 659938 の反応式
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

参加物

8

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 83717Copper iodide触媒HCID 178418476HCID 178418476、化合物触媒HCID 6228Dimethylformamide溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-4951c305bfd4457389ec8e82d453e684
出典データセット
uspto-grants-2011_12
特許番号
US08084395B2

関連ノート

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