Sodium hydride → HCID 16073827, compound

Participants

Reaction Steps

To a suspension of NaH (60% dispersion in oil, 11.1 mg) in 2.5 mL anhydrous DMF is added N-(4-chlorobenzyl)-8-fluoro-4-hydroxy-6-(hydroxymethyl)-3-quinolinecarboxamide from Preparation No. 7 (100 mg). After stirring the reaction mixture at room temperature for 15-20 min., 2-(3-bromopropoxy)tetrahydro-2H-pyran (89.4 mg) is added. The reaction is stirred at room temperature for 3 days. The reaction mixture is treated with saturated aqueous NaHCO3, then extracted with CH2Cl2 (3×). The combined organic layers are washed with 15% K2CO3 and H2O (2×), dried over Na2SO4, and condensed to obtain a yellow residue. The residue is chromatographed eluting with 2% MeOH in CH2Cl2. Fractions homogenous by TLC are combined and condensed to afford 34.0 mg (24%) of the title compound as a white solid.

Provenance & Evidence