Sodium Iodide → 2-(4-Chlorophenyl)imidazo(1,2-a)pyridine-3-acetonitrile

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Reaction Steps

30.0 g of molecular sieves were activated under vacuum, at 100° C., for 1 h. 5.00 g of 3-(chloromethyl)-2-(4-chlorophenyl)imidazo[1,2-a]pyridine hydrochloride (15.94 mmol, 1 eq), 9.38 g of NaCN (191.3 mmol, 12 eq), 428 mg of Bu4NCN (1.59 mmol, 0.1 eq), 9.56 g of NaI (63.77 mmol, 4 eq) and 150 mL of ACN were added. The mixture were stirred at RT, O/N. Sieves were filtered and washed with EtOAc. The filtrate was washed twice with NaHCO3, dried on MgSO4, filtered and concentrated to give 4.95 g of crude. It was purified by silica gel chromatography (MeOH/CH2Cl2, 0 to 5%) and gave two batches: batch #01 (very pure)=3.90 g, batch #02 (some impurities) was purified on activated carbon to give 0.90 g. Total yield=82%. m/e+=268 (M+H+).

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