HCID 117635644, compound → HCID 117635649, compound

Participants

Reaction Steps

(S)-Ethyl 5-(4,4-dimethylpiperidin-1-yl)-6-(1-hydroxy-2-methoxy-2-oxoethyl)-7-methylimidazo[1,2-a]pyridine-2-carboxylate (1.3 g, 3.22 mmol, 1 equiv) was suspended in DCM (3 mL) and tert-butyl acetate (10 mL). To this mixture was added 70% HClO4 (0.831 mL, 9.67 mmol, 3 equiv) through sealed rubber stopper. After 2 h, LCMS indicated about 60% conversion. The reaction was washed with 1 N NaOH, dried (Na2SO4), and concentrated in vacuo. The crude product was purified via silica gel flash chromatography (0-100% EtOAc [2% TEA]/hexane) to provide the product (0.68 g, 46%). 1H NMR (400 MHz, CDCl3) 8.22 (d, J=0.8 Hz, 1H), 7.31 (s, 1H), 6.02 (s, 1H), 4.47 (q, J=7.2 Hz, 2H), 3.70 (s, 3H), 3.60 (td, J=11.4, 2.8 Hz, 1H), 3.49 (td, J=11.5, 2.6 Hz, 1H), 3.10 (dt, J=11.9, 3.5 Hz, 1H), 2.95-2.86 (m, 1H), 2.44 (d, J=1.0 Hz, 3H), 1.73-1.48 (m, 7H), 1.45 (t, J=7.0 Hz, 4H), 1.24 (s, 10H), 1.15 (s, 3H), 1.08 (s, 3H); LCMS (ESI, M+1): 502.35.

Provenance & Evidence