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

HRID 1271564

반응식

HRID 1271564 반응식
[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

참가 물질

6

반응물 2

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

생성물 1

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

시약·촉매·용매 3

HCID 178418476HCID 178418476, 화합물촉매HCID 6344Dichloromethane용매HCID 8471Triethylamine용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-99b7ae33a07f4627bf712d9e7b4b48c1
출처 데이터셋
uspto-grants-2007_04
특허 번호
US07205411B2

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