2-Bromopyridine → HCID 71563077, compound

Participants

Reaction Conditions

Reaction Steps

4-(5-Chloroquinoline-2-yl)-2-methylbut-3-yn-2-ol (24.5 mg, 0.0997 mmol), PdCl2(PPh3)2 (3.4 mg, 0.00484 mmol), CuI (1.2 mg, 0.00875 mmol), and KOH (44.6 mg, 0.795 mmol) were dissolved in diisopropylamine (0.2 mL) in a vial. The resulting mixture was stirred for 5 min under nitrogen atmosphere, followed by adding 2-bromopyridine (9.6 uL, 0.0997 mmol) thereto. After the vial was capped, it was heated to 110° C. The completion of the reaction was confirmed by TLC (EtOAc/Hexane=1:1). When the reaction was completed, the reactant was cooled down to room temperature and filtered through Celite and ethyl acetate. The thus obtained filtrate was extracted with ethyl acetate, to thereby obtain an organic layer. The organic layer was dried over anhydrous MgSO4 and filtered. The filtrate was concentrated under reduced pressure and purified by column chromatography (EtOAc/Hexane=1:1, R.f: 0.3), to thereby obtain 5-chloro-2-(pyridine-2-ylethynyl)quinoline (6.2 mg, 25%) as a brown solid.

Provenance & Evidence