1,2-dimethyl-1H-imidazole-5-carbaldehyde → (4-Chloro-2-methoxy-3-(4-(trifluoromethyl)benzyl)quinolin-6-yl)(1,2-dimethyl-1H-imidazol-5-yl)methanol

Participants

Reaction Conditions

Reaction Steps

To a 50 mL flask containing 6-bromo-4-chloro-2-methoxy-3-(4-(trifluoromethyl)benzyl)quinoline (2 g, 4.64 mmol, Intermediate 47: step d) was added THF (25 mL) at room temperature which resulted in a colorless homogeneous mixture. The solution was cooled to −70° C. which remained homogeneous and then n-BuLi (2.5 M in hexanes, 1.8 mL, 4.5 mmol) was added drop wise. The color of the solution became a dark reddish-brown color. After 1 minute, 1,2-dimethyl-1H-imidazole-5-carbaldehyde (710 mg, 5.72 mmol in 4 mL THF) was introduced and the color of the mixture became greenish to light orange all within 1 minute. The mixture was allowed to warm to 0° C. over 45 minutes at which time the reaction was quenched with aqueous NH4Cl solution. The reaction was diluted further with water and extracted with EtOAc (3×45 mL). The combined organics were washed with brine, dried over MgSO4, filtered and concentrated to give a pale yellow solid. The solid was triturated with Et2O and collected by filtration and rinsed with additional Et2O and dried to afford the title compound as a white powder.

Provenance & Evidence