Benzyl Bromide → 3-(1-benzyl-1H-imidazol-4-yl)pyridine

Participants

Reaction Steps

To a solution of 34 (35 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. Benzyl bromide (26 μL, 0.32 mmol) was added and the resultant solution was stirred for 10 min. The reaction was quenched by the slow addition of HCl(aq) (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 fraction was adjusted to pH 9 with NaOH(aq) (10 N). The organic fraction was collected and the aqueous 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=0.26) to afford the title compound 60 (43 mg, 74% yield) as a white semisolid: 1H NMR (CDCl3) δ 8.95 (br s, 1H), 8.47 (br s, 1H), 8.10 (m, 1H) 7.64 (m, 1H) 7.42-7.17 (m, 7H) 5.17 (s, 2H); LRMS (ESI) m/z calcd for C15H14N3 [M+H]+ 236. found 236; HRMS (ESI) m/z calcd for C15H14N3 [M+H]+ 236.1188. found 236.1198; HPLC>99% (tR=10 min, 60 (A):40 (B): 0.02 (C); tR=6.12 min, 60 (A):40 (B): 0.07 (C)).

Provenance & Evidence