1,2-Dichloroethane → 4-(4-Chlorophenyl)-N-(6-fluoro-1H-indazol-5-yl)-2-methyl-6-oxo-1,4,5,6-tetrahydro-3-pyridinecarboxamide

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Reaction Steps

The product of Example 4 Step 2 (240 mg, 0.903 mmol, 1.00 equiv), 5-amino-6-fluoroindazole (137 mg, 0.903 mmol, 1.0 equiv), and EDC (207 mg, 1.084 mmol, 1.20 equiv) were suspended in 2.0 mL DMF. Et3N (0.151 mL, 1.084 mmol, 1.2 equiv) was added and the solution was stirred at room temperature for 18 hrs. The reaction mixture was diluted with EtOAc and 1N HCl. The phases were separated, and the organic phase was washed twice with 1N HCl, once with satd. NaHCO3, and once with satd. NaCl. The organic phase was dried over Na2SO4, filtered, and concentrated en vacuo. The residue was purified by flash chromatography (20-100% EtOAc in Hexanes) to provide 83 mg (23%) of the title compound as an off white solid. MS (ES+) m/e 399 [M+H]+

Provenance & Evidence