Dimethylformamide → [2-(6-Fluoropyridin-2-yl)-imidazol-1-yl]acetic acid tert-butyl ester

Participants

Reaction Steps

A mixture of 2-Fluoro-6-(1H-imidazol-2-yl)pyridine (410 mg; 2.51 mmol), tert-butyl bromoacetate (539 mg; 2.76 mmol), potassium carbonate (520 mg; 3.77 mmol), and N,N-dimethylformamide (20 mL) is stirred at room temperature for 16 h. Water (60 mL) is added and the mixture extracted with ethyl acetate (3×70 mL). The organic extracts are washed with water (3×40 mL) and brine (1×40 mL), dried (MgSO4), and concentrated to give [2-(6-Fluoropyridin-2-yl)-imidazol-1-yl]acetic acid tert-butyl ester as an orange oil (630 mg). 1H NMR (CDCl3) δ 8.12 (dd,1H), 7.82(q,1H), 7.16(s,1H), 6.98(s,1H), 6.81(dd,1H), 5.14(s,2H), 1.44s,(9H), LCMS: 276.1(M−).

Provenance & Evidence