Cesium carbonate → N-[6-chloro-4-(1H-pyrrolo[2,3-b]pyridin-3-yl)pyridin-2-yl]pentanamide

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A mixture of Example 7a (82.5 mg, 0.204 mmol), pentanamide (28.9 mg, 0.286 mmol), cesium carbonate (100 mg, 0.306 mmol), palladium (II) acetate (2.29 mg, 10.2 μmol), and Xantphos (8.86 mg, 0.015 mmol) was degassed and heated at 85° C. in a sealed vial for 6 hours. The reaction mixture was cooled and concentrated. The residue was treated with 20% brine and extracted with EtOAc (2×). The organic layers were dried and concentrated. The crude intermediate was dissolved in dioxane (1.5 mL) and treated with 20% sodium hydroxide (0.15 mL, 0.20 mmol). The mixture was heated at 50° C. for 2 hours. The solvent was evaporated. The residue was treated with water, sonicated, filtered, and washed with water, and purified by reverse-phase HPLC as described in Example 56 to give the title compound (8.0 mg) as trifluoroacetic acid salts. 1H NMR (500 MHz, DMSO-d6) ppm 0.90 (t, J=7.48 Hz, 3H), 1.27-1.38 (m, 2H), 1.54-1.64 (m, 2H), 2.43 (t, J=7.32 Hz, 2H), 7.29 (m, 1H), 7.57 (s, 1H), 8.28-8.37 (m, 3H), 8.60 (s, 1H), 10.74 (s, 1H), 12.36 (s, 1H). MS (ESI+) m/z 328.9 (M+H)+.

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