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

HRID 1271564

Reaktionsgleichung

Reaktionsgleichung von HRID 1271564
[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

Komponenten

6

Edukt 2

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418476HCID 178418476, VerbindungKatalysatorHCID 6344DichloromethaneLösungsmittelHCID 8471TriethylamineLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-99b7ae33a07f4627bf712d9e7b4b48c1
Quelldatensatz
uspto-grants-2007_04
Patentnummer
US07205411B2

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