3-Chlorophenol → [2-(3-Chloro-phenoxy)-5-fluoro-pyridin-3-yl]-(3,4-dihydro-2H-quinolin-1-yl)-methanone

Participants

Reaction Conditions

Reaction Steps

To a solution of (2-chloro-5-fluoro-pyridin-3-yl)-(3,4-dihydro-2H-quinolin-1-yl)-methanone (53.2 mg, 0.18 mmol, 1.0 equiv) and 3-chloro-phenol (23.5 mg, 0.18 mmol, 1.0 equiv; [CAS RN 108-43-0]) in acetonitrile (1 mL) was added potassium carbonate (50.7 mg, 0.37 mmol, 2.0 equiv; [CAS RN 584-08-7]), copper(I) iodide (3.5 mg, 0.018 mmol, 0.1 equiv; [CAS RN 7681-65-4]) and copper(0) nanopowder with an averaged particle size of 100 nm (3.5 mg, 0.055 mmol, 0.3 equiv; [CAS RN 7440-50-8]). The reaction mixture was heated by microwave irradiation to 200° C. for 90 min. Removal of the solvent under reduced pressure and purification by preparative HPLC on reversed phase (Xterra® PrepMSC 18, 5 μm, 19×50 mm column equipped with a Gilson Liquid Handler 215 autosampler, two Rainin Dynamax® SD-300 pumps, a Sedex ELSD 75 lightscatter and a Dionex UVD 340S UV detector) eluting with a gradient of acetonitrile/water provided 4.3 mg (6%) of the title compound. MS (ISP): 383.2 [M+H]+.

Provenance & Evidence