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

Participants

Reaction Steps

The product of Example 3, Step 2 (50 mg, 0.176 mmol, 1.00 equiv), 5-amino-3-methylindazole (26 mg, 0.176 mmol, 1.0 equiv), and EDC (41 mg, 0.212 mmol, 1.20 equiv) were suspended in 0.5 mL DMF. Et3N (0.030 mL, 0.212 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 20 mg (27%) of the title compound as an off white solid. MS (ES+) m/e 413 [M+H]+

Provenance & Evidence