Triethylamine → 6-(7-Azabicyclo[2.2.1]heptan-7-yl)-4-methylpyridin-3-amine

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Reaktionsgleichung

F[C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([N+:9]([O-])=O)=[CH:4][N:3]=1.Cl.[CH:13]12[NH:19][CH:16]([CH2:17][CH2:18]1)[CH2:15][CH2:14]2.C(N(CC)CC)C>C(#N)C>[CH:16]12[N:19]([C:2]3[N:3]=[CH:4][C:5]([NH2:9])=[C:6]([CH3:8])[CH:7]=3)[CH:13]([CH2:18][CH2:17]1)[CH2:14][CH2:15]2

Komponenten

Reaktionsbedingungen

Temperatur: 80 °C

Versuchsvorschrift

To a solution of 2-fluoro-4-methyl-5-nitropyridine (150 mg, 0.96 mmol) in acetonitrile (5 mL) was added 7-azabicyclo[2.2.1]heptane hydrochloride (153 mg, 1.15 mmol) and triethylamine (335 μL, 2.40 mmol). The reaction was heated at 80° C. for 16 h. The reaction was quenched with water (2 mL) and solvent was evaporated. The residue was dissolved in ethyl acetate (15 mL), washed with 1N HCl (10 mL), dried over MgSO4, filtered and concentrated in vacuo to afford 6-(7-azabicyclo[2.2.1]heptan-7-yl)-4-methylpyridin-3-amine (160 mg, 71% yield) as yellow solid which was used in next step without purification. 1H NMR (400.0 MHz, CDCl3) δ 8.96 (s, 1H), 6.37 (s, 1H), 4.59 (s, 2H), 2.59 (d, J=0.4 Hz, 3H), 1.83-1.80 (m, 4H), 1.61-1.54 (m, 4H).

Aufarbeitung

customThe reaction was quenched with water (2 mL) and solvent
customwas evaporated
dissolutionThe residue was dissolved in ethyl acetate (15 mL)
washwashed with 1N HCl (10 mL)
dry with materialdried over MgSO4
filtrationfiltered
concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag: ord-61778505f3504c5c96b67bedb266f5cc
Quelldatensatz: uspto-grants-2013_02
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08367660B2

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