Electric Literature of 64119-42-2, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 64119-42-2, name is Ethyl 6-chloro-5-cyano-2-methylpyridine-3-carboxylate, molecular formula is C10H9ClN2O2, The compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.
A solution of 7 (0.090 g, 0.4 mmol), tert-butyl hexahydropyrrolo[3,4-c]pyrrole-2(1H)-carboxylate (0.093 g, 0.44 mmol) and TEA (0.202 g, 2.0 mmol) in EtOH (2 mL) was heated in a microwave oven at 120 C for 20 minutes. The mixture was concentrated and the crude was purified by flash chromatography (heptane/EtOAc 3:1). Yield: 0.088 g (55%). 1H NMR (400MHz, CDCl3): 1.35 (3H, t, J = 7.1 Hz), 1.44 (9H, s), 2.68 (3H, s), 2.92-3.02 (2H, m), 3.24-3.35 (2H,m), 3.56-3.69 (2H, m), 3.72-3.79 (2H, m), 4.03-4.13 (2H, m), 4.28 (2H, q, J = 7.1 Hz), 8.30 (1H, s). MS m/z: 401 (M+1). tert-Butyl 5-[3-cyano-5-(ethoxycarbonyl)-6-methylpyridin-2-yl]hexahydropyrrolo[3,4-c]pyrrole-2(1H)-carboxylate (0.085 g, 0.21 mmol) was dissolved in TFA/DCM 1:1 (2 mL) and the reaction mixture was stirred at rt for 30 minutes and then concentrated. The crude material was dissolved in DCM (1 mL). TEA (0.106 g, 1.05 mmol) and benzenesulfonyl isocyanate (0.042 g, 0.23 mmol) were added at 0 C. The reaction mixture was stirred at 0 C for 10 minutes and then at rt for 1.5 h. The mixture was concentrated and the crude was purifed by reverse phase HPLC. Yield: 0.075 g (74%).
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Reference:
Article; Bach, Peter; Bostroem, Jonas; Brickmann, Kay; Van Giezen; Groneberg, Robert D.; Harvey, Darren M.; O’Sullivan, Michael; Zetterberg, Fredrik; European Journal of Medicinal Chemistry; vol. 65; (2013); p. 360 – 375;,
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