3-Bromopyridine → HCID 63902396, compound

Participants

Reaction Conditions

Reaction Steps

To toluene (2.2 mL), n-butyllithium (a 2.77 mol/L solution in hexane, 0.82 mL, 2.28 mmol) was added under a nitrogen atmosphere at −60° C. To this, a solution of 3-bromopyridine (200 μL, 2.08 mmol) in toluene (0.73 mL) was slowly added dropwise at the same temperature and the mixture was stirred at −78° C. for 15 minutes. To this suspension, tetrahydrofuran (0.73 mL) was slowly added dropwise and the mixture was stirred at the same temperature for 15 minutes. Then, 4-formyltetrahydropyran (285 mg, 2.50 mmol) was added thereto. Over 1 hour, the reaction mixture was heated to −15° C. Then, a saturated aqueous ammonium chloride solution was added to the reaction mixture, and extraction with ethyl acetate was performed, followed by washing with brine and drying over anhydrous sodium sulfate. The solvent was evaporated off under reduced pressure, and the residue was purified by silica gel column chromatography (chloroform/methanol=19/1) to give 3-[hydroxy(tetrahydropyran-4-yl)methyl]pyridine (Compound CW) (353 mg, yield: 88%).

Provenance & Evidence