3-Ethynylpyridine → (6-Methyl-2-pyridin-3-ylethynyl-pyridin-3-yl)amine

HRID 1271560

Reaktionsgleichung

Reaktionsgleichung von HRID 1271560
Br[C:2]1[C:7]([NH2:8])=[CH:6][CH:5]=[C:4]([CH3:9])[N:3]=1.[C:10]([C:12]1[CH:13]=[N:14][CH:15]=[CH:16][CH:17]=1)#[CH:11]>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>[CH3:9][C:4]1[N:3]=[C:2]([C:11]#[C:10][C:12]2[CH:13]=[N:14][CH:15]=[CH:16][CH:17]=2)[C:7]([NH2:8])=[CH:6][CH:5]=1

Komponenten

5

Edukt 2

HCID 1860033-EthynylpyridineHCID 144180512-Bromo-6-methylpyridin-3-amine

Produkt 1

HCID 10353036(6-Methyl-2-pyridin-3-ylethynyl-pyridin-3-yl)amineAusbeute 49 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418476HCID 178418476, VerbindungKatalysatorHCID 8471TriethylamineLösungsmittel

Versuchsvorschrift

Following the same procedure as described in Example 1, (2-bromo-6-methyl-pyridin-3-yl)amine (200 mg, 1.07 mmol) reacted with (PPh3)2PdCl2 (37 mg, 0.05 mmol), Cul (10 mg, 0.05 mmol) and 3-ethynyl-pyridine (110 mg, 1.07 mmol) in triethylamine (1.6 ml). The crude residue was purified by flash chromatography (DCM-DCM/MeOH 97:3) to yield 100 mg (0.48 mmol, 49%) of (6-methyl-2-pyridin-3-ylethynyl-pyridin-3-yl)amine as a yellow powder. The hydrochloride of (6-methyl-2-pyridin-3-ylethynyl-pyridin-3-yl)amine was prepared as described in Example 1 to yield after trituration with pentane 145 mg (100%) of the title hydrochloride as a yellow solid.

Aufarbeitung

  1. customThe crude residue was purified by flash chromatography (DCM-DCM/MeOH 97:3)

Quellen und Nachweise

ORD-Eintrag
ord-7cb582cbc27a4bc793c3f5db30ec7735
Quelldatensatz
uspto-grants-2007_04
Patentnummer
US07205411B2

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