2,5-Dichlorophenol → [3-(2,5-Dichloro-phenoxy)-pyridin-4-yl]-(2,3-dihydro-benzo[1,4]oxazin-4-yl)-methanone

Beteiligte Stoffe

Reaktionsbedingungen

Reaktionsschritte

To a solution of (3-bromo-pyridin-4-yl)-(2,3-dihydro-benzo[1,4]oxazin-4-yl)-methanone (80 mg, 0.25 mmol, 1.0 equiv) and 2,5-dichloro-phenol (49 mg, 0.30 mmol, 1.2 equiv; [CAS RN 583-78-8]) in anhydrous toluene (1.5 mL) was added caesium carbonate (204 mg, 0.63 mmol, 2.5 equiv; [CAS RN 534-17-8]) and tetrakis(acetonitrile)copper(I) hexafluorophosphate (18.7 mg, 0.050 mmol, 0.2 equiv; [CAS RN 64443-05-6]). The reaction mixture was heated by microwave irradiation to 160° C. for 2 h. 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 17 mg (17%) of the title compound as a light brown solid. MS (ISP): 400.9 [M+H]+.

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