Hydrochloric Acid → 3-(1-ethylimidazol-4-yl)pyridine

Participants

Reaction Steps

To a solution of 34 (36 mg, 0.25 mmol) in THF (5 mL) under argon was added sodium hydride (12 mg, 0.29 mmol) in one portion and the resultant slurry was stirred for 20 min. Iodoethane (26 μL, 0.32 mmol) was added and the resultant solution was stirred for 10 min. The reaction was stopped by the careful addition of aqueous hydrochloric acid (1 N, 2 mL), diluted with 13 mL of water and washed with ethyl acetate (3×15 ml). Dichloromethane was added (25 mL) and the aqueous was adjusted to pH 9 with NaOH(aq) (10 N). The organic fraction was collected and the aqueous fraction was extracted with dichloromethane (20 mL), the combined organic fractions were dried (Na2SO4), filtered and the solvent was removed in vacuo. The crude material was chromatographed on silica gel (CH3OH/CHCl3, 2.5/97.5, Rf=0.27) to afford the title compound 59 (34 mg, 79% yield) as a clear oil: 1H NMR (CDCl3) δ 8.93 (m, 1H), 8.44 (m, 1H), 8.07 (m, 1H), 7.54 (br s, 1H), 7.28 (m, 2H), 4.02 (q, J=7.4 Hz, 2H), 1.49 (t, J=7.4 Hz, 3H); LRMS (ESI) m/z calcd for C10H11N3 [M+H]+ 174. found 174; HRMS (ESI) m/z calcd for C10H11N3 [M+H]+ 174.1031. found 174.1042; HPLC>97% (tR=13.28 min, 60 (A):40 (B): 0.02 (C); tR=3.67 min, 80 (A):20 (B): 0.1 (C).

Provenance & Evidence