Ammonium Chloride → HCID 10047221, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 7-{6-[4-(trifluoromethyl)phenyl]pyrimidin-4-yloxy}quinoline-3-carbaldehyde, (Example 60b), (220 mg, 0.56 mmol) in anhydrous THF (10 mL) was magnetically stirred under N2 in a −78° C. bath while methylmagnesium bromide (0.22 mL, 0.66 mmol, 3.0 M in Et2O, Aldrich) was added quickly. The reaction mixture was stirred at −78° C. for 5 min, then treated with satd NH4Cl (5 mL). The bath was removed and the mixture was stirred for 5 min, then diluted with EtOAc (60 mL) and washed with satd NH4Cl (20 mL), water (20 mL), satd NaHCO3 (20 mL), satd NaCl (20 mL), dried over Na2SO4, filtered and concentrated in vacuum. Purification by silica gel chromatography (gradient: 60-85% EtOAc in hexanes) provided the title compound as an off-white solid. Mp: 156-157° C. MS (ESI, pos. ion.) m/z: 412 (M+1). Anal. Calcd for C22H16F3N3O2: C, 64.23; H, 3.92; N, 10.21; F, 13.85. Found: C, 63.99; H, 4.05; N, 10.01; F, 13.63.

Provenance & Evidence