Ether, bis(1-chloroethyl) → 6-Chloro-5-methoxymethoxy-nicotinonitrile

To a solution of 6-chloro-5-hydroxy-nicotinonitrile (1.12 g, 7.24 mmol) in DCM (15 mL) was added N,N-diisopropyl ethylamine (1.57 mL, 9.05 mmol) followed by the addition of chloro-methyl methylether (0.66 mL, 8.69 mmol) slowly at 0° C. After overnight at room temperature, the reaction mixture was washed with saturated NaHCO3 (10 mL) and brine (10 mL), dried over Na2SO4, filtered, and concentrated to give yellow oil. Purification was accomplished by flash chromatography on silica gel using 5-25% EtOAc/hexanes gradient elution to yield the title compound (0.68 g, 50%) as a transparent oil. 1H NMR (400 MHz, DMSO-d6) δ ppm 8.53 (d, J=2.0 Hz, 1H), 8.14 (d, J=2.0 Hz, 1H), 5.42 (s, 2H), 3.40 (s, 3H); MS (ES) m/z: 199 (M+1)+.

1. washthe reaction mixture was washed with saturated NaHCO3 (10 mL) and brine (10 mL)
2. dry with materialdried over Na2SO4
3. filtrationfiltered
4. concentrationconcentrated
5. customto give yellow oil
6. customPurification
7. washwas accomplished by flash chromatography on silica gel using 5-25% EtOAc/hexanes gradient elution

ORDレコード

ord-e0d1dfe446ee40ada479bcd9fc7d1703

出典データセット

uspto-grants-2016_08

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US09416146B2