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Stage #1: With n-butyllithium In diethyl ether at -78 - -70℃; for 0.5 h; Stage #2: at -78 - 20℃; for 1.5 h;
To a 3 L 3-neck flask was added Et2O followed by 2-chloro-6-methyl-5- bromopyridine (56.97 g, 0.28 mol). The mixture was cooled to -78 0C and n-BuLi (132 mL, 0.33 mol) was added dropwise with an addition funnel while maintaining the pot temperature below -70 0C. The mixture was agitated at -78 0C for 30 min, DMF (43 mL, 0.56 mol) was added dropwise at -78 0C then the cooling bath was removed and the reaction was agitated at rt for 1.5 h and quenched with brine (300 mL). The layers were separated and the aqueous layer was extracted with Et2O (150 mL). The combined organic layers were neutralized with cone. HCl to pH -3-4 followed by saturated aqueous NaHCO3 (300 mL). The layers were separated and the organic layer was concentrated to dryness. The product was recrystallized from Et2O/hexane (200 mL, 1 : 1) to afford a light yellow crystalline solid (19 g). The filtrate was concentrated and purified by column chromatography (EtOAc/hexane, 1 :9) to give another crop of product (13 g). Combined yield was 71percent. 1H NMR (CDCl3) δ 2.87 (s, 3H), 7.35 (d, IH, J= 9.0 Hz), 8.07 (d, IH, J= 9.0 Hz), 10.31 (s, IH).
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