3-Bromopyridine → 2-Fluoro-4-(1-hydroxy-1-pyridin-3-yl-methyl)-benzonitrile

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Reaction Conditions

Reaction Steps

3-Bromopyridine (1.40 g, 8.86 mmol) was dissolved in anhydrous Et2O (15 mL). The solution was cooled to −78° C., treated with a 1.6 M solution of n-BuLi (5.53 mL, 8.86 mmol), and stirred for 15 min. The lithium solution was cannulated into a −78° C. solution of 2-fluoro-4-formyl-benzonitrile (Example 1, Step D) in THF (15 mL) and stirred for 15 min. The reaction was quenched with H2O, partitioned between CH2Cl2 and saturated NaHCO3 solution and separated. The aqueous layer was washed with CH2Cl2 (2×), the organic layers combined, dried (Na2SO4), filtered and concentrated to give the title compound after chromatography on SiO2 eluting with 0-3% MeOH/CH2Cl2 w/NH4OH.

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