Sodium bis(trimethylsilyl)amide → 3-Bromo-5-(oxetan-3-YL)pyridine

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To a vial were added (5-bromopyridin-3-yl)boronic acid (110 mg, 0.544 mmol), nickel iodide (5.10 mg, 0.016 mmol), trans-2-aminocyclohexanol hydrochloride (2.473 mg, 0.016 mmol), sodium bis(trimethylsilyl)amide (100 mg, 0.544 mmol) and 2-propanol (0.5 mL). The reaction was stirred under nitrogen for 10 minutes prior to addition of a solution of 3-iodooxetane (50 mg, 0.27 mmol) in 2-propanol (0.2 mL). The vial was sealed and heated at 80° C. overnight. The reaction was then filtered through celite with the aid of ethanol. The solution was concentrated and purified by flash chromatography on silica gel (10-100% ethyl acetate in hexanes) to provide the title compound: LCMS m/z 215.90 [M+2+H]+; 1H NMR (500 MHz, CD3OD) δ 8.56 (s, 1H), 8.51 (s, 1H), 8.19 (s, 1H), 5.11-5.08 (m, 2H), 4.72-4.70 (m, 2H), 4.34-4.29 (m, 1H).

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