Cesium carbonate → (R)-methyl 5-(sec-butylamino)-4-cyano-2-methylbenzoate

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To a solution of methyl 4-cyano-5-iodo-2-methylbenzoate (500 mg, 1.66 mmol) in 1,4-dioxane (25 mL) was added 9,9-dimethyl-4,5-(bis(diphenylphosphino)xanthene (96 mg, 0.166 mmol), tris(dibenzylideneacetone)-dipalladium (76 mg, 0.083 mmol), cesium carbonate (1.08 g, 3.32 mmol) and (R)-butan-2-amine (506 μL, 4.98 mmol). The reaction mixture was heated to 95° C. and stirred for 16 h, at which time it was cooled to room temperature. The heterogeneous mixture was filtered through a bed of celite, and the filter cake rinsed with ethyl acetate. The filtrate was concentrated, and the residue was purified by flash chromatography (100% hexanes to 5% ethyl acetate in hexanes) to afford (R)-methyl 5-(sec-butylamino)-4-cyano-2-methylbenzoate (300 mg, 73%) as a bright yellow oil. MS (EI) for C14H18N2O2: 247 (MH+).

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