1-Ethynyl-4-fluorobenzene → (2-(4-Fluoro-phenylethynyl)-6-methyl-pyridin-3-yl)amine

HRID 1271561Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1271561
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:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=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>[F:18][C:15]1[CH:16]=[CH:17][C:12]([C:10]#[C:11][C:2]2[C:7]([NH2:8])=[CH:6][CH:5]=[C:4]([CH3:9])[N:3]=2)=[CH:13][CH:14]=1

Komponenten

5

Edukt 2

HCID 5226271-Ethynyl-4-fluorobenzeneHCID 144180512-Bromo-6-methylpyridin-3-amine

Produkt 1

HCID 10105101(2-(4-Fluoro-phenylethynyl)-6-methyl-pyridin-3-yl)amineAusbeute 68 %

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 (36 mg, 0.05 mmol), Cul (10 mg, 0.05 mmol) and 1-ethynyl-4-fluorobenzene (184 μl, 1.07 mmol) in triethylamine (5 ml). The crude residue was purified by flash chromatography (hexane/ethyl acetate 7:3) to yield 164 mg (0.72 mmol, 68%) of (2-(4-fluoro-phenylethynyl)-6-methyl-pyridin-3-yl)amine as a yellow solid. The hydrochloride of (2-(4-fluoro-phenylethynyl)-6-methyl-pyridin-3-yl)amine was prepared as described in Example 1 to yield after trituration with ethyl acetate 154 mg (0.51 mmol, 71%) of the title hydrochloride as a yellow solid.

Aufarbeitung

  1. customThe crude residue was purified by flash chromatography (hexane/ethyl acetate 7:3)

Quellen und Nachweise

ORD-Eintrag
ord-de93a11a11624ec396a2bc8655c1a0a6
Quelldatensatz
uspto-grants-2007_04
Patentnummer
US07205411B2

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