5-Fluoro-3-pyridinamine → HCID 68157950, Verbindung

Beteiligte Stoffe

Reaktionsbedingungen

Reaktionsschritte

To a solution of 5-Fluoropyridin-3-ylamine (1.22 g, 10.9 mmol) in THF (30 mL) at −0° C. was added potassium tert-butoxide (2.43 g, 21.7 mmol) and the reaction mixture stirred at 0° C. for 10 min. This solution was added via cannula to a solution of 2,6-difluoro-3-nitrobenzonitrile (2 g, 10.9 mmol) in THF (20 mL) at −78° C. and the dark purple reaction mixture stirred at −78° C. for 10 min. The reaction mixture was diluted with water and extracted with EtOAc (3×30 mL). The combined organic fractions were washed with brine, dried (MgSO4), concentrated in vacuo. The resultant residue was subjected to flash chromatography (SiO2, eluting with 0-100% EtOAc in cyclohexane). The solid obtained was triturated with pentane to give the title compound as an orange solid (1.73 g, 58%). 1H NMR 400 MHz δ (CDCl3): 9.73 (1H, br s), 8.53 (1H, dd, J=9.5, 5.7 Hz), 8.47 (1H, d, J=2.5 Hz), 8.43-8.40 (1H, m), 7.33 (1H, dt, J=8.8, 2.2 Hz), 6.83 (1H, dd, J=9.5, 7.3 Hz).

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