Sodium Hydroxide → 7-({2-[(4-Methoxybenzyl)(methyl)amino]pyridin-4-yl}oxy)-1,2,3,4-tetrahydronaphthalene-2-carboxylic acid

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A solution of 7-[(2-chloropyridin-4-yl)oxy]-1,2,3,4-tetrahydronaphthalene-2-carboxylic acid (1.50 g, 4.94 mmol) and 1-(4-methoxyphenyl)-N-methylmethanamine (2.24 g, 14.8 mmol) in NMP (9 mL) was heated in a sealed tube at 150° C. for 40 hr. The reaction mixture was allowed to cool to rt and diluted with water and 1N HCl solution. The pH was adjusted to 4 by the addition of 1N NaOH solution. The mixture was extracted with EtOAc (3×) and the organic solutions were combined, washed with water and brine, dried over Na2SO4 and concentrated. The residue was purified by column chromatography to give 7-({2-[(4-methoxybenzyl)(methyl)amino]pyridin-4-yl}oxy)-1,2,3,4-tetrahydronaphthalene-2-carboxylic acid as an off-white solid (581 mg, 28.1%). LCMS: (FA) ES+ 419.2, ES− 417.2.

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