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レコード

ord-e6887193b9374998b7127e48606ff0f5

出典データセット

uspto-grants-2008_07

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US07396840B2