Potassium Iodide → [2-(3-Cyano-phenyl)-1-methyl-ethyl]-carbamic acid tert-butyl ester

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To a sealed pressure tube was added [2-(3-bromo-phenyl)-1-methyl-ethyl]-carbamic acid tert-butyl ester (1.23 g, 3.9 mmol), sodium cyanide (250 mg, 5.1 mmol), potassium iodide (130 mg, 0.8 mmol), N-N′-dimethylethylenediamine (0.41 mL, 3.9 mmol), and toluene (6 mL). This suspension was then sparged with nitrogen prior to adding copper iodide (150 mg, 0.8 mmol). Reaction mixture heated to 130° C. for 16 h while stirring. Reaction partitioned between ethyl acetate and 30% aqueous ammonia. Organic washed with saturated ammonium chloride, then dried over magnesium sulfate. Reaction reduced to an oil under vacuum and isolated as a white solid after purification on silica. M+1=261.

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