[F:1][C:2]1[CH:3]=[C:4]([C:9]2[C:10]3[N:11]([N:15]=[C:16]([NH2:18])[N:17]=3)[CH:12]=[CH:13][CH:14]=2)[CH:5]=[CH:6][C:7]=1[F:8].C1COCC1.II.[Mg]>CO>[F:1][C:2]1[CH:3]=[C:4]([CH:9]2[CH2:14][CH2:13][CH2:12][N:11]3[N:15]=[C:16]([NH2:18])[N:17]=[C:10]23)[CH:5]=[CH:6][C:7]=1[F:8]
To a solution of 8-(3,4-difluorophenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-amine (prepared in analogy to example 66a-c, 500 mg, 2.03 mmol) in methanol (60 mL) and THF (30 mL) magnesium (395 mg, 16.2 mmol) and iodine (3 mg) were added. After 1.5 hours at room temperature further magnesium (395 mg, 16.2 mmol) was added and the reaction mixture was stirred at 50° C. for 1 hour. Further magnesium (148 mg, 6.09 mmol) was added again and stirred at room temperature for 4 hours. The solvent was evaporated, the residue was dissolved in THF and dried over Na2SO4. The solvent was evaporated and the residue was purified by flash chromatography (silica gel, 100 g, 0% to 15% MeOH/NH3 (9:1) in dichloromethane, 45 minutes). The title compound was obtained as white solid (226 mg, 45%).
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