HCID 59375369, Verbindung → HCID 59375367, Verbindung

HRID 2193012Notizen

Reaktionsgleichung

[Cl:1][C:2]1[N:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[C:4]1[CH:16]=[N:15][CH:14]=[CH:13][C:5]=1[C:6](Cl)=[N:7]2.[CH:17]([Mg]Br)([CH3:19])[CH3:18]>C1COCC1.C1C=CC(P(C2C=CC=CC=2)CCP(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Cl-].[Cl-].[Ni+2]>[Cl:1][C:2]1[N:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[C:4]1[CH:16]=[N:15][CH:14]=[CH:13][C:5]=1[C:6]([CH:17]([CH3:19])[CH3:18])=[N:7]2

Komponenten

Reaktionsbedingungen

Temperatur: -10 °C

Versuchsvorschrift

To a solution of 1,6-dichloropyrido[4,3-c]-1,6-naphthyridine (50 mg, 0.200 mmol) and 1,2-bis(diphenylphosphino)ethanenickel(II) chloride (1.056 mg, 1.999 μmol) in THF (0.4 mL). The mixture was cooled to −10° C. in a methanol-ice bath, and isopropylmagnesium bromide (220 μl 0.220 mmol, 1 M in THF) was added dropwise. The reaction mixture was stirred at −10° C. for 30 min. The mixture was then allowed to warm to room temperature and then stirred for 30 min. The reaction mixture was quenched with aqueous ammonium chloride (saturated), and the aqueous layer was extracted with ethyl acetate. The combined organic extracts were dried over sodium sulfate and concentrated under reduced pressure to afford 1-chloro-6-isopropylpyrido[4,3-c]-1,6-naphthyridine as a red solid. LRMS (APCI) calc'd for (C14H13ClN3) [M+H]+, 258.1; found 258.0.

Aufarbeitung

temperatureto warm to room temperature
stirringstirred for 30 min
customThe reaction mixture was quenched with aqueous ammonium chloride (saturated)
extractionthe aqueous layer was extracted with ethyl acetate
dry with materialThe combined organic extracts were dried over sodium sulfate
concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag: ord-3e0d4e46cef9472f943db13e06e4b100
Quelldatensatz: uspto-grants-2012_12
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08329722B2

Notizen zur Reaktion

Wird geladen…