Potassium Carbonate → 2-Methyl-6-[(3R)-3-[(2S)-2-methylpyrrolidin-1-yl]pyrrolidin-1-yl]-3-nitro-pyridine

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To a solution of (2R,3′S)-2-methyl-[1,3′]bipyrrolidinyl dihydrochloride (1.59 g, 7 mmol) in DMSO (24 mL) was added K2CO3 (3.87 g, 28 mmol) and 2-chloro-6-methyl-5-nitropyridine (1.81 g, 10.5 mmol) and then heated to 90° C. for 8 hours. The reaction was cooled to rt and NaHCO3 (aq) (200 mL) was added. The solution was extracted with EtOAc (2×250 mL). The combined organic extracts were washed with NaHCO3 (aq) (200 mL), H2O (200 mL), and brine (150 mL), dried over K2CO3, filtered and concentrated to obtain a residue which was then purified by flash column chromatography (0% to 5% MeOH/CH2Cl2) to afford 2 g of the title compound.

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