3-Iodobenzonitrile → 3-(3-Amino-6-methyl-pyridin-2-ylethynyl)-benzonitrile

HRID 1271566Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1271566
[C:1]([C:3]1[C:8]([NH2:9])=[CH:7][CH:6]=[C:5]([CH3:10])[N:4]=1)#[CH:2].I[C:12]1[CH:13]=[C:14]([CH:17]=[CH:18][CH:19]=1)[C:15]#[N:16]>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>[NH2:9][C:8]1[C:3]([C:1]#[C:2][C:12]2[CH:13]=[C:14]([CH:17]=[CH:18][CH:19]=2)[C:15]#[N:16])=[N:4][C:5]([CH3:10])=[CH:6][CH:7]=1

Komponenten

5

Edukt 2

HCID 1443413-IodobenzonitrileHCID 184547762-Ethynyl-6-methylpyridin-3-amine

Produkt 1

HCID 100142073-(3-Amino-6-methyl-pyridin-2-ylethynyl)-benzonitrileAusbeute 27,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418476HCID 178418476, VerbindungKatalysatorHCID 8471TriethylamineLösungsmittel

Versuchsvorschrift

To a solution of Cul (2.4 mg, 12 μmol) in triethylamine (4 ml) were added (2-ethynyl-6-methyl-pyridin-3-yl)amine (33 mg, 0.33 mmol described in Example 7), (PPh3)2PdCl2 (8.8 mg, 12 μmol), and 3-iodobenzonitrile (57 mg, 0.25 mmol). The reaction mixture was stirred at room temperature for 48 h. The solvent was evaporated and the crude residue was purified by flash chromatography (cyclohexane/ethyl acetate 1:1) to yield 16 mg (69 μmol, 21%) of 3-(3-amino-6-methyl-pyridin-2-ylethynyl)-benzonitrile as a pale yellow solid.

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-92d5f57175884a58a8477232874a4618
Quelldatensatz
uspto-grants-2007_04
Patentnummer
US07205411B2

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