2-Bromo-5-fluoropyridine → 1-[2-(2-Dimethylamino-ethyl)-benzo[b]thiophen-3-yl]-1-(5-fluoro-pyridin-2-yl)-ethanol

Participants

Reaction Conditions

Reaction Steps

2-Bromo-5-fluoropyridine (5 g, 0.03 mol) was dissolved in methylene chloride (18 mL) and was cooled at −78° C. 1.6 M of n-butyllithium in hexane (18 mL) was added dropwise in 5 minutes and the reaction was stirred for 120 minutes at −78° C. Then a solution of 1-[2-(2-dimethylamino-ethyl)-benzo[b]thiophen-3-yl]-ethanone (1.75 g, 7.1 mmol) dissolved in methylene chloride (9 mL) and added dropwise and the mixture was allowed to warm to room temperature gradually overnight. The reaction was quenched with aq NH4Cl, followed by water and ammonium hydroxide. The organic layer was extracted with Methylene chloride, and dried over sodium sulfate. Silica gel column chromatography (eluent: 9:1 DCM/MeOH) afforded 1.656 g of 1-[2-(2-dimethylamino-ethyl)-benzo[b]thiophen-3-yl]-1-(5-fluoro-pyridin-2-yl)-ethanol (Compound 7-1) (68%).

Provenance & Evidence