Triethylamine → HCID 59305309, compound

Participants

Reaction Steps

In a CEM snap top microwave vial were combined 1-Difluoromethoxy-4-ethynyl-benzene (1.48 g, 8.80 mmol), [3-(3-Bromo-phenyl)-cyclobutylidene]-acetic acid ethyl ester (2.00 g, 6.78 mmol), Copper iodide (232 mg, 0.131 mmol), Tetrakis(triphenylphosphine)palladium (470 mg, 1155.56 g/mol, 0.046 mmol), and triethylamine (20 g, 198 mmol). The capped vial was placed in a CEM Explorer microwave instrument and irradiated for 30 minutes at 80° C. The crude reaction mixture and dichloromethane washings were poured directly onto silica gel. Purification by column chromatography (isocratic; 5% EtOAc in hexanes) afforded an oil 1.42 g (55%). 1H NMR (400 MHz, DMSO-d6) δ ppm 1.20 (t, J=7.2 Hz, 3H) 2.94-3.03 (m, 1H) 3.06-3.16 (m, 1H) 3.19-3.28 (m, 1H) 3.49-3.60 (m, 1H) 3.62-3.72 (m, 1H) 4.08 (q, J=7.2 Hz, 2H) 5.68-5.78 (m, 1H) 7.06-7.32 (m, 3H) 7.39 (dd, J=8.8, 3.7 Hz, 3H) 7.46-7.52 (m, 1H) 7.62 (d, J=8.8 Hz, 2H); MS (ES) m/z 383.1 [M+H]+.

Provenance & Evidence