2-Ethynyl-6-methylpyridin-3-amine → (2-(5-Fluoro-pyridin-3-ylethynyl)-6-methyl-pyridin-3-yl)amine

HRID 1271565

Reaktionsgleichung

Reaktionsgleichung von HRID 1271565
[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:13]=[N:14][CH:15]=[C:16](I)[CH:17]=1>C(N(CC)CC)C.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]=[N:14][CH:13]=1

Komponenten

5

Edukt 2

HCID 184547762-Ethynyl-6-methylpyridin-3-amineHCID 184547783-Fluoro-5-iodopyridine

Produkt 1

HCID 10036674(2-(5-Fluoro-pyridin-3-ylethynyl)-6-methyl-pyridin-3-yl)amineAusbeute 22 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418476HCID 178418476, VerbindungKatalysatorHCID 8471TriethylamineLösungsmittel

Versuchsvorschrift

To a solution of Cul (11 mg, 0.06 mmol) in triethylamine (5 ml) were added (2-ethynyl-6-methyl-pyridin-3-yl)amine (40 mg, 0.30 mmol, described in Example 7), (PPh3)2PdCl2 (21 mg, 0.06 mmol), and 3-fluoro-5-iodopyridine (111 mg, 0.45 mmol). The reaction mixture was stirred at room temperature for 14 h. The solvent was evaporated. The crude residue was purified by flash chromatography (cyclohexane/ethyl acetate 7:3) to yield 15 mg (66 μmol, 22%) of (2-(5-fluoro-pyridin-3-ylethynyl)-6-methyl-pyridin-3-yl)amine as a yellow solid.

Aufarbeitung

  1. customThe solvent was evaporated
  2. customThe crude residue was purified by flash chromatography (cyclohexane/ethyl acetate 7:3)

Quellen und Nachweise

ORD-Eintrag
ord-bf9e5549b426412f821840f0bbe51ebc
Quelldatensatz
uspto-grants-2007_04
Patentnummer
US07205411B2

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