Cl[C:2]1[N:7]=[C:6]([C:8]#[N:9])[CH:5]=[C:4]([C:10]2[CH:15]=[C:14]([O:16][CH2:17][CH3:18])[CH:13]=[CH:12][C:11]=2[F:19])[CH:3]=1.CN1C(=O)[CH2:24][CH2:23][CH2:22]1.C([Mg]Cl)(C)C>C1COCC1.CCOCC>[CH2:17]([O:16][C:14]1[CH:13]=[CH:12][C:11]([F:19])=[C:10]([C:4]2[CH:3]=[C:2]([CH:23]([CH3:24])[CH3:22])[N:7]=[C:6]([C:8]#[N:9])[CH:5]=2)[CH:15]=1)[CH3:18]A mixture of 6-chloro-4-(5-ethoxy-2-fluoro-phenyl)pyridine-2-carbonitrile (which may be prepared as described in Description 113) (1.5 g, 5.42 mmol) NMP (2.61 mL, 27.07 mmol) and Fe(acac)3 (95.73 mg, 0.2700 mmol) in THF (27.106 mL) was stirred at 0° C. and treated with 2M isopropyl magnesium chloride in THF (7.59 mmol) and the mixture was stirred at 0° C. for 30 mins. The mixture was diluted with ether (200 ml) and quenched with brine. The product was extracted into ether (3x) and the extracts were dried (Na2SO4) and evaporated. The product was purified by flash chromatography (0-100% DCM in isohexane) to give 4-(5-ethoxy-2-fluoro-phenyl)-6-isopropyl-pyridine-2-carbonitrile (D114) as a white solid;
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