2-Bromopyridine → HCID 21706291, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of n-butyllithium (2.5 M/hexane, 0.98 mL, 2.46 mmol) in THF (7 mL) at −78° C. was added 2-bromopyridine (0.235 mL, 2.46 mmol) dropwise. The mixture was stirred at −78° C. for 1 hr. This solution was added via cannula to a solution of 4-bromo-3-fluorobenzaldehyde (as described in Example 20, Step A) (0.5 g, 2.46 mmol) in THF (5 mL) at −78° C. The resulting solution was stirred at −78° C. for 15 min. and at 25° C. for 2 hr. The reaction was cooled to 0° C. and quenched with saturated NH4Cl. The mixture was partitioned with EtOAc and the organic layer was washed with water, brine and dried over MgSO4. The solvents were removed in vacuo to obtain the title compound after chromatography (silica gel, CH2Cl2:MeOH 99:1).

Provenance & Evidence