Sodium hydride → HCID 57987621, compound

Participants

Reaction Steps

To a solution of methyl 3-[2-(2,6-dichlorophenyl)-6-quinolinyl]-2-hydroxypropanoate 55 (0.159 g) and α-bromo-2,6-dichlorotoluene (1.05 g) in DMF (3.5 ml) is added 17 mg of NaH (60% dispersion in mineral oil) and Ag2O (0.102 g). The solution is stirred for 1 night at room temperature. A saturated solution of NaHCO3 is added. The aqueous phase is extracted with AcOEt (3×10 ml). The organic phases are washed with water (2×10 ml), with brine and dried over MgSO4. After concentration, the residue is purified twice over silica gel using AcOEt/petroleum ether 10/90 then 15/85 as eluent to give methyl 2-[(2,6-dichlorobenzyl)oxy]-3-[2-(2,6-dichlorophenyl)-6-quinolinyl]propanoate 56.

Provenance & Evidence