Reaktionsgleichung
C([Li])CCC.[Cl:6][C:7]1[CH:12]=[CH:11][N:10]=[C:9]([NH2:13])[CH:8]=1.[CH:14]1([C:17]2[CH:18]=[N:19][CH:20]=[C:21]([CH:24]=2)[C:22]#[N:23])[CH2:16][CH2:15]1>O1CCCC1>[Cl:6][C:7]1[CH:12]=[CH:11][N:10]=[C:9]([NH:13][C:22](=[NH:23])[C:21]2[CH:24]=[C:17]([CH:14]3[CH2:16][CH2:15]3)[CH:18]=[N:19][CH:20]=2)[CH:8]=1Komponenten
Edukt 3
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- -40 °C
Versuchsvorschrift
n-Butyllithium (1.6 M, 2.2 mL, 0.0034 mol) was added slowly for a period of 5 min to a solution of 4-chloropyridin-2-amine (0.4 g, 0.0031 mol) in anhydrous tetrahydrofuran (20 mL) at −78° C. The reaction temperature was raised to −40° C. and stirred for 15 min. The reaction mixture was cooled to −78° C. and 5-cyclopropylnicotinonitrile (0.45 g, 0.0031 mol) in tetrahydrofuran (5 mL) was added. The temperature was raised to RT and stirred it for 3 h. The reaction mixture was quenched with a saturated aqueous ammonium chloride solution (25 mL) then extracted with ethyl acetate (2×50 mL). The combined organic layers were dried over sodium sulphate and concentrated under vacuum to afford the crude product, which was recrystalised with a DCM and ether mixture to afford the title compound. MS (M−1): 271.0.
Aufarbeitung
- temperatureThe reaction mixture was cooled to −78° C.
- temperatureThe temperature was raised to RT
- stirringstirred it for 3 h
- customThe reaction mixture was quenched with a saturated aqueous ammonium chloride solution (25 mL)
- extractionthen extracted with ethyl acetate (2×50 mL)
- dry with materialThe combined organic layers were dried over sodium sulphate
- concentrationconcentrated under vacuum
- customto afford the crude product, which
- customwas recrystalised with a DCM and ether mixture
Quellen und Nachweise
- ORD-Eintrag
- ord-d8c3e655819a4365bb6868c4d24a8396
- Quelldatensatz
- uspto-grants-2015_11
- Patentnummer
- US09193724B2
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