Yield:118412-66-1 82%

Reaction Conditions:

Stage #1: (4-fluorophenyl)(3-pyridinyl)methanonewith N,N,N,N,N,N-hexamethylphosphoric triamide in dichloromethane at 25; for 0.166667 h;Inert atmosphere;
Stage #2: with trichlorosilane in dichloromethane at 25; for 24 h;Inert atmosphere;

Steps:

3.1. Reduction of Pyridines and N-Heteroaromatics

General procedure: Under an argon atmosphere, pyridine 1 or N-heteroaromatic 3 (0.10 mmol) and HMPA (3.5 mg,0.02 mmol) were added in anhydrous DCM (0.7 mL) and stirred at room temperature for 10 min, andthen trichlorosilane (2.0 M, 0.3 mL) was added. The reaction was stirred at room temperature for 24h, quenched with H2O, and then the pH was adjusted to ~7-8 with saturated NaHCO3. The mixturewas extracted with EtOAc (3 × 5 mL). The combined organic layers were washed with brine, driedover anhydrous Na2SO4, concentrated under reduced pressure and purified with columnchromatography (silica gel, DCM/MeOH/TEA = 10/1/0.1) to afford a pure product.

References:

Fu, Yun;Sun, Jian [Molecules,2019,vol. 24,# 3,art. no. 401]