C([Li])CCC.[Cl:6][C:7]1[N:12]=[C:11]([F:13])[C:10]([O:14][CH2:15][O:16][CH3:17])=[CH:9][CH:8]=1.[Br:18][C:19]1[CH:20]=[CH:21][C:22]([F:27])=[C:23]([CH:26]=1)[CH:24]=[O:25].[Cl-].[NH4+]>C1COCC1.CCOC(C)=O.O>[Br:18][C:19]1[CH:20]=[CH:21][C:22]([F:27])=[C:23]([CH:24]([C:9]2[CH:8]=[C:7]([Cl:6])[N:12]=[C:11]([F:13])[C:10]=2[O:14][CH2:15][O:16][CH3:17])[OH:25])[CH:26]=1DIPA (0.750 mL, 5.35 mmol) was dissolved in dry THF (20 mL) under nitrogen and cooled in a dry ice bath to −78° C. Butyllithium solution (2.5 M in hexanes, 2.0 mL, 5.00 mmol) was added and the solution was stirred for a few minutes. A solution of 6-chloro-2-fluoro-3-(methoxymethoxy)pyridine (0.864 g, 4.51 mmol) in dry THF (10 mL) was added slowly and the resulting solution stirred for 40 minutes. A solution of 5-bromo-2-fluorobenzaldehyde (1.02 g, 5.05 mmol) in dry THF (1 mL) was added dropwise. After 10 minutes saturated ammonium chloride (10 mL), water (100 mL) and EtOAc (100 mL) were added and the phases mixed and separated. The organic was dried with magnesium sulfate and evaporated to dryness under reduced pressure. Purification using silica chromatography (hexane to EtOAc gradient) gave the desired (5-bromo-2-fluorophenyl)(6-chloro-2-fluoro-3-(methoxymethoxy)pyridin-4-yl)methanol.
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