Cl.[C:2]1([C:8]#[C:9][C:10]2[CH:11]=[C:12]([CH:16]=[N:17]O)[CH:13]=[N:14][CH:15]=2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+].C(Cl)(Cl)Cl.[F:25][C:26]([F:31])([F:30])[C:27]([OH:29])=[O:28]>[Zn]>[F:25][C:26]([F:31])([F:30])[C:27]([OH:29])=[O:28].[F:25][C:26]([F:31])([F:30])[C:27]([OH:29])=[O:28].[C:2]1([C:8]#[C:9][C:10]2[CH:11]=[C:12]([CH2:16][NH2:17])[CH:13]=[N:14][CH:15]=2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1Add zinc dust (0.39 g, 6.04 mmol) in small portions to a solution of 5-phenylethynyl-pyridine-3-carbaldehyde oxime hydrochloride, (prepared as described in EXAMPLE 6), (0.16 g, 0.60 mmol) in trifluoroacetic acid (1.4 mL) while keeping the internal reaction temperature between about 15-20° C. using a chilled water bath. After 15 min, add a 1:1 mixture of 2 N sodium hydroxide and chloroform, while stirring vigorously and cooling in an ice bath. Filter away the solids and wash the filtrate with water, an aqueous saturated solution of sodium chloride, dry (magnesium sulfate), filter and concentrate. Purify the residue by reverse phase HPLC, eluting with 5:95 to 100:0 acetonitrile:water with 0.02% trifluoroacetic acid, to give the title compound as pale yellow solid (0.015 g, 11.9%).
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