Cesium carbonate → (6-Methyl-pyridin-2-yl)-[1,7]naphthyridin-8-yl-amine

HRID 1787587

Reaktionsgleichung

Reaktionsgleichung von HRID 1787587
Cl[C:2]1[N:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[CH:9][CH:8]=[CH:7]2.[NH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([CH3:19])[N:14]=1.C1(P(C2C=CC=CC=2)C2C3OC4C(=CC=CC=4P(C4C=CC=CC=4)C4C=CC=CC=4)C(C)(C)C=3C=CC=2)C=CC=CC=1.C(=O)([O-])[O-].[Cs+].[Cs+]>O1CCOCC1>[CH3:19][C:15]1[N:14]=[C:13]([NH:12][C:2]2[N:3]=[CH:4][CH:5]=[C:6]3[C:11]=2[N:10]=[CH:9][CH:8]=[CH:7]3)[CH:18]=[CH:17][CH:16]=1

Komponenten

6

Edukt 4

HCID 10796Cesium carbonateHCID 157652-Amino-6-methylpyridineHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 123427128-Chloro-(1,7)naphthyridine

Produkt 1

HCID 16118550(6-Methyl-pyridin-2-yl)-[1,7]naphthyridin-8-yl-amine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
150 °C

Versuchsvorschrift

8-Chloro-[1,7]naphthyridine (Example A) (0.2 g, 1.2 mmol) and 2-amino-6-methylpyridine (0.13 g, 1.2 mmol) were dissolved in 8 ml dry dioxane. 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (145 mg, 0.24 mmol), cesium carbonate (0.63 g, 1.95 mmol) and tri(dibenzylideneacetone)dipalladium chloroform complex (0.13 g, 0.12 mmol) were added and the reaction mixture was stirred under microwave irradiation for 50 minutes at 150° C. The reaction mixture was then evaporated and purified by flash chromatography on silica gel (heptane/ethyl acetate 95:5->70:30 gradient). The desired product was obtained as a light yellow solid (98 mg, 34%),

Aufarbeitung

  1. customThe reaction mixture was then evaporated
  2. custompurified by flash chromatography on silica gel (heptane/ethyl acetate 95:5->70:30 gradient)

Quellen und Nachweise

ORD-Eintrag
ord-5937f0fba58341699293691ccde86743
Quelldatensatz
uspto-grants-2009_03
Patentnummer
US07511055B2

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