Ethyl Acetate → 2-Benzyloxy-4-(2-chloro-4-methoxy-phenyl)-3-nitro-pyridine

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Reaction Steps

To a solution of 2-benzyloxy-4-chloro-3-nitro-pyridine (Wilde, et al. WO 99/01454, which is incorporated herein by reference) (3.0 g, 11.3 mmol) in ethanol (10 mL) and toluene (40 mL), was added Na2CO3 (14.17 mL, 2 M), 2-chloro-4-methoxyphenylboronic acid (3.17 g, 17.0 mmol), and Pd(PPh3)2Cl2 (0.48 g, 0.68 mmol) and the mixture was heated at reflux for 5 h. The reaction was cooled and poured into EtOAc and H2O (500 mL). The EtOAc layer was washed with H2O, brine, dried (Na2SO4), filtered and concentrated in vacuo. Purification using flash chromatography (10% EtOAc-Hexane) gave 1.51 g (36%) of 2-benzyloxy-4-(2-chloro-4-methoxy-phenyl)-3-nitro-pyridine as a viscous oil: MS (AP) m/z 370.8 [(M+H)+, 100].

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