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Heck reaction

A stirred mixture of (R)-indan-l-yl-(6-vinyl-4H-benzo[d][l,3]oxazin-2-yl)-amine (250 mg, 0.86 mmol), 3-bromopyridine (177 mg, 1.12 mmol), tri(o-tolyl)phosphine (21 mg, 0.07 mmol), triethylamine (261 mg, 2.58 mmol) and palladium acetate (7.73 mg, 0.034 mmol) in N,N-dimethylformamide (3 ml) was heated in a sealed tube at 100°C for 3 h. The reaction mixture was poured into water (20 ml), extracted with ethyl acetate (2 x 40 ml). The combined organic layers were washed with water (2 x 20 ml) and brine (20 ml), dried (magnesium sulfate) and evaporated. Further purification by flash chromatography (ethyl acetate/ heptane) on silica gel and crystallization (dichloromethane/ heptane) yielded the title compound as yellow solid (70 mg, 22%).


Patent reference: WO2010026110 (Roche)