Water → HCID 57556189, compound

Participants

Reaction Steps

1,3,5-Trichlorotriazine (94 mg, 510 μmol) was added to dimethylformamide (0.04 mL, 510 μmol) at 25° C. After the formation of a white solid (10 min), DCM (3 mL) was added, followed by 1-(8-chloro-2-(3-fluorophenyl)quinolin-3-yl)ethanol (140.0 mg, 464 μmol), made from procedure K. After the addition, the mixture was stirred at room temperature for 4 h. Water (10 mL) was added, and then diluted with DCM (10 mL), the organic phase was washed with 15 mL of a saturated solution of NaHCO3, followed by water and brine. The organic layers were dried and concentrated. Purification of the residue by flash chromatography over silica gel, using 10% hexane in EtOAc, gave 8-chloro-3-(1-chloroethyl)-2-(3-fluorophenyl)quinoline, Mass Spectrum (ESI) m/e=320.0 (M+1).

Provenance & Evidence