Triethylamine → 2-Cyano-3-fluoropyridine

To a solution of 3-fluoropyridine 1-oxide (1.21 g, 10.7 mmol) in CH3CN (10 mL) was added Et3N (4.4 mL, 31.6 mmol) followed by TMSCN (4.3 mL, 32.2 mmol) and the reaction was stirred at reflux for 6.5 hours. The mixture was diluted with CH2Cl2 (100 mL) and washed with saturated aqueous NaHCO3 (50 mL). The aqueous layer was extracted with CH2Cl2 (3×40 mL) and the combined organic layers were dried (Na2SO4), filtered and concentrated to give a crude dark red oil. Purification of the crude material by column chromatography on silica gel (CH2Cl2/MeOH, 98:2) afforded the title compound as a yellow solid (1.01 g, 77%). 1H NMR (CDCl3): δ 7.58–7.67 (m, 2H), 8.54–8.57 (m, 1H).

1. temperatureat reflux for 6.5 hours
2. washwashed with saturated aqueous NaHCO3 (50 mL)
3. extractionThe aqueous layer was extracted with CH2Cl2 (3×40 mL)
4. dry with materialthe combined organic layers were dried (Na2SO4)
5. filtrationfiltered
6. concentrationconcentrated
7. customto give a crude dark red oil
8. customPurification of the crude material by column chromatography on silica gel (CH2Cl2/MeOH, 98:2)

ORD record

ord-6d7df6fce5eb41f7a498dfec62199b0a

Source dataset

uspto-grants-2006_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07084155B2