N,N'-Dimethylethylenediamine → (5-Phenylethynyl-pyridin-3-yl)-carbamic acid tert-butyl ester

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Reaction Steps

Stir a mixture of 3-bromo-5-phenylethynyl-pyridine, (prepared as described in EXAMPLE 9), (2.5 g, 10 mmol), copper (I) iodide (0.190 g, 1 mmol), potassium carbonate (2.76 g, 20 mmol), carbamic acid tert-butyl ester (1.17 g, 10 mmol), N,N′-dimethylethylenediamine (0.220 mL, 2 mmol) in 1,4-dioxane (10 mL) at 110° C. in a sealed tube for 36 h. Cool to room temperature and concentrate. Purify by silica gel chromatography, eluting with 100:0 dichloromethane:methanol to 90:10 dichloromethane:methanol, and then crystallizing from ethyl acetate to give the title compound (430 mg, 15%).

Provenance & Evidence