1,3-Difluoro-5-iodobenzene → (2-(3,5-Difluoro-phenylethynyl)-6-methyl-pyridin-3-yl)amine

HRID 1271564

反応式

HRID 1271564 の反応式
[C:1]([C:3]1[C:8]([NH2:9])=[CH:7][CH:6]=[C:5]([CH3:10])[N:4]=1)#[CH:2].[F:11][C:12]1[CH:17]=[C:16](I)[CH:15]=[C:14]([F:19])[CH:13]=1>C(N(CC)CC)C.C(Cl)Cl.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>[F:11][C:12]1[CH:17]=[C:16]([C:2]#[C:1][C:3]2[C:8]([NH2:9])=[CH:7][CH:6]=[C:5]([CH3:10])[N:4]=2)[CH:15]=[C:14]([F:19])[CH:13]=1

参加物

6

反応物 2

HCID 27782211,3-Difluoro-5-iodobenzeneHCID 184547762-Ethynyl-6-methylpyridin-3-amine

生成物 1

HCID 10332058(2-(3,5-Difluoro-phenylethynyl)-6-methyl-pyridin-3-yl)amine収率 58%

試薬・触媒・溶媒 3

HCID 178418476HCID 178418476、化合物触媒HCID 6344Dichloromethane溶媒HCID 8471Triethylamine溶媒

実験手順

To a solution of Cul (4.3 mg, 23 μmol) in triethylamine (5 ml) were added (2-ethynyl-6-methyl-pyridin-3-yl)amine (60 mg, 0.45 mmol), (PPh3)2PdCl2 (16 mg, 23 μmol), and 1,3-difluoro-5-iodobenzene (109 mg, 0.45 mmol). The reaction mixture was stirred at room temperature for 20 h. The solvent was evaporated to afford a brown oil which was taken up in DCM and the solution was washed with water. The aqueous phase was extracted twice with DCM. The organic phases were dried over Na2SO4, filtered and concentrated. The crude residue was purified by flash chromatography (hexane/ethyl acetate 7:3) to yield 64 mg (0.26 mmol, 58%) of (2-(3,5-difluoro-phenylethynyl)-6-methyl-pyridin-3-yl)amine as a yellow solid.

後処理

  1. customThe solvent was evaporated
  2. customto afford a brown oil which
  3. washthe solution was washed with water
  4. extractionThe aqueous phase was extracted twice with DCM
  5. dry with materialThe organic phases were dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe crude residue was purified by flash chromatography (hexane/ethyl acetate 7:3)

出典と根拠

ORDレコード
ord-99b7ae33a07f4627bf712d9e7b4b48c1
出典データセット
uspto-grants-2007_04
特許番号
US07205411B2

関連ノート

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