Phenol → N-(1-Benzyl-6-phenoxy-1,2,3,4-tetrahydroquinolin-3-yl)benzenesulfonamide

Participants

Reaction Conditions

Reaction Steps

A suspension of 87B (55 mg, 0.12 mmol), phenol (33.9 mg, 0.36 mmol), K2CO3 (50 mg, 0.36 mmol) and copper iodide (17.1 mg, 0.09 mmol) in DMF (1.0 mL) was heated at 200° C. in a sealed tube with stirring for 16 h. After cooling to RT, the reaction mixture was filtered, the filtrate purified using preparative HPLC (YMC S5 ODS 20×100 mm) eluting with MeOH (70-100%) in H2O for 8 min, and then 100% MeOH in H2O for 7 min to give the title compound (4 mg) as a light brownish solid. HPLC: 91% at 6.99 min (retention time) (Conditions: Zorbax SB C18 (4.6×75 mm); Eluted with 0% to 100% B, 8 min gradient. (A=90% H2O−10% MeOH−0.1% H3PO4 and B=10% H2O−90% MeOH−0.1% H3PO4); Flow rate at 2.5 mL/min. UV detection at 220 nm). MS (ES): m/z 471 [M+H]+.

Provenance & Evidence