Reaktion #626762

Reaktionsgleichung

oxetan-3-amine

triethylamine

2-bromo-5-cyanopyridine

→

6-(oxetan-3-ylamino)nicotinonitrile

Ausbeute 25.0%

Lösungsmittel

isopropanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe vial was capped
2. 2
   Sonstigeirradiated in a microwave oven at 120° C. for 5 h
3. 3
   SonstigeThe reaction mixture was partitioned between ethyl acetate (10 mL) and water (10 mL)
4. 4
   WaschenThe organic layer was washed with brine
5. 5
   Trocknendried over Na2SO4
6. 6
   Sonstigethe solvent was removed under reduced pressure
7. 7
   SonstigeThe resulting crude product was purified by column chromatography over silica gel (chloroform/MeOH, 0-5% EtOAc)

Vorschrift

In a microwave vial, oxetan-3-amine (125 mg, 1.736 mmol), triethylamine (526 mg, 5.21 mmol) were added to a solution of 2-bromo-5-cyanopyridine (317 mg, 1.736 mmol) in isopropanol (3 mL). The vial was capped and irradiated in a microwave oven at 120° C. for 5 h. The reaction mixture was partitioned between ethyl acetate (10 mL) and water (10 mL). The organic layer was washed with brine, dried over Na2SO4 and the solvent was removed under reduced pressure. The resulting crude product was purified by column chromatography over silica gel (chloroform/MeOH, 0-5% EtOAc) to afford 75 mg (25%) of 6-(oxetan-3-ylamino)nicotinonitrile (I-25) as an off-white solid. 1H NMR (400 MHz, DMSO) δ 8.36 (s, 1H), 7.58-7.61 (dd, J=1.9, 6.9 Hz, 1H), 6.39 (d, J=8.7 Hz, 2H), 5.37 (br. s, 1H), 4.91-5.06 (m, 3H), 4.54-4.57 (m, 2H); ESI-LC/MS (m/z): [M+H]+ 176.2, RT 1.65 min.

Quelle