Potassium Carbonate → Ethyl 4-(4-chloro-3-(dibutylcarbamoyl)-5-methyl-1H-pyrazol-1-yl)-3-(1,2,3,4-tetrahydroisoquinoline-2-carbonyl)benzoate

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To a solution of ethyl 4-fluoro-3-(1,2,3,4-tetrahydroisoquinoline-2-carbonyl)benzoate (645 mg, 1.97 mmol) and N,N-dibutyl-4-chloro-5-methyl-1H-pyrazole-3-carboxamide (1.07 g, 3.94 mmol) in NMP (9.9 mL) was added K2CO3 (1.09 g, 7.88 mmol). The resulting reaction mixture was stirred at 125° C. for 3 h, cooled to room temperature and quenched with 10% aq. LiCl solution. The solution was extracted with EtOAc (3×) and the combined organic extracts were washed with 10% LiCl (3×), dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified by flash chromatography (25% EtOAc/CHCl3) to afford the title compound (930 mg, 81%). 1H NMR (DMSO-d6, 2:1 mixture of amide rotamers) δ 8.32 (s, 0.5H), 8.23-8.13 (m, 1H), 8.11-8.00 (m, 1H), 7.76-7.87 (m, 0.5H), 7.28-7.08 (m, 3.5H), 7.03-6.94 (m, 0.5H), 4.87-4.51 (m, 2H), 4.43-4.27 (m, 2.5H), 3.86-3.75 (m, 0.5H), 3.63-3.32 (m, 3H), 3.23-3.07 (m, 1H), 3.05-2.94 (m, 1H), 2.85-2.62 (m, 2H), 2.27 (s, 2H), 2.22 (s, 1H), 1.48-1.09 (m, 9H), 1.04-0.92 (m, 2H), 0.90-0.82 (m, 3H), 0.70-0.63 (m, 3H); MS(ESI+) m/z 579.4 (M+H)+.

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