Sodium Bicarbonate → Fluoro-quinolin-6-yl-acetonitrile

Beteiligte Stoffe

Reaktionsschritte

A solution of quinolin-6-yl-acetonitrile (1.06 g, 6.3 mmol) in tetrahydrofuran (40 mL) was cooled to −78° C. to which tert-butyl lithium (0.8 M in pentane, 7.6 mmol, 7.9 mL) was added in a dropwise fashion over 10 minutes. After the addition was complete the mixture was stirred at −78° C. for 30 min before a solution of N-fluorodi(benzenesulfonyl)-amine (1.5 eq., 9.45 mmol, 3.0 g) in tetrahydrofuran (10 mL) was added. The reaction mixture was stirred for 2 hours at −78° C. before water was added followed by aqueous NaHCO3. The mixture was extracted with dichloromethane (3×80 mL), dried (Na2SO4) and concentrated in vacuo onto silica gel and purified via flash column chromatography (SiO2, hexane:ethyl acetate 100/0-50/50) to return the title compound as a red solid (520 mg, 2.8 mmol, 44%). 1H NMR 500 MHz (DMSO-d6) δ 6.05 (1H, d), 7.66 (1H, dd), 7.95 (1H, dd), 8.19 (1H, d), 8.32 (1H, t), 8.55 (1H, d), 9.03 (1H, dd); MS (m/z) 187 [M+H+]+.

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