3-Acetyl-6-methylpyridine → 1-(6-Methylpyridin-3-yl)-2-(4-(methylsulfonyl)phenyl)ethanone

Participants

Reaction Conditions

Reaction Steps

A Schlenk reaction tube anhydrified beforehand provided with magnetic anchor was loaded with tri-tert-butyl-phosphonium tetrafluoborate (5.4 mg; 18.5 μmol), Pd(OAc)2 (2.1 mg; 9.2 μmol), 4-bromophenylmethylsulfone (130.4 mg; 0.55 mmol), 1-(6-methylpyridin-3-yl)ethanone of formula (II) (50 mg; 0.37 mmol) and was closed with a septum. The vessel was degassed by 3 argon cycles, then 2 ml anhydrous toluene were added with a syringe. T-BuOK (165.7 mg; 1.48 mmol) was added in portions and the solution was heated to 80° C. for 16 hours. The mixture was diluted with a saturated solution of NaHCO3 (20 mL) and extracted with AcOEt (3×20 mL). The combined organic phases were washed with an aqueous solution saturated with NaHCO3 (20 mL), anhydrified on MgSO4 and concentrated in a vacuum. The residue was purified by flash chromatography using AcOEt/cyclohexane as eluent in a gradient from 5:5 to 10:0. 32.1 mg product were obtained, for a molar yield of 30% as a white crystalline solid.

Provenance & Evidence