4-(5-bromo-2-fluorophenyl)morpholine

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a CEM snap top microwave vial (10 ml) equipped with a magnetic stir bar (3×10 mm) was added 4-(5-bromo-2-fluorophenyl)morpholine (390 mg, 1.50 mmol) in triethylamine (1.5 mL). Copper iodide (12 mg, 0.060 mmol), Tetrakis(triphenylphosphine) palladium (35 mg, 0.030 mmol) and triisopropylsilyl-acetylene (0.390 mg, 2.14 mmol) were added at room temperature. The reaction was capped and irradiated in a CEM Explorer microwave at 80° C. for 30 minutes then forced air-cooled. The crude material was loaded onto silica gel and chased with dichloromethane. Purification by chromatography (hexanes) afforded 540 mg of an oil (quant); 1H NMR (400 MHz, DMSO-d6) δ ppm 1.06-1.10 (m, 21H) 3.00 (t, J=4.6 Hz, 4H) 3.71 (t, J=4.6 Hz, 4H) 7.01 (dd, J=8.5, 2.0 Hz, 1H) 7.08 (ddd, J=4.9, 2.9, 2.6 Hz, 1H) 7.11-7.18 (m, 1H); MS (ES) m/z 362.2 [M+H]+ To a CEM snap top microwave vial (10 ml) equipped with a magnetic stir bar (3×10 mm) The reaction was capped irradiated in a CEM Explorer microwave at 80° C. for 30 minutes then forced air-cooled Purification by chromatography (hexanes)

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a CEM snap top microwave vial (10 ml) equipped with a magnetic stir bar (3×10 mm) was added 5-Bromo-2-fluoroaniline (1.00 g, 5.26 mmol), sodium iodide (2.37 gm, 15.8 mmol), potassium carbonate (1.45 gm, 10.5 mmol), and 2-chloroethyl ether (1.30 gm, 9.09 mmol) in dimethylformamide (6.5 mL). The reaction was capped and irradiated in a CEM Explorer microwave at 120° C. for 4 hours then forced air-cooled. Purification by column chromatography [default gradient (ISCO); EtOAc/hexanes] afforded 397 mg (29%) an oil; 1H NMR (400 MHz, DMSO-d6) δ ppm 3.00 (t, J=1.7 Hz, 4H) 3.69-3.73 (m, 4H) 7.10-7.15 (m, 3H); MS (EI) m/z 259.0 [M+·]. To a CEM snap top microwave vial (10 ml) equipped with a magnetic stir bar (3×10 mm) The reaction was capped irradiated in a CEM Explorer microwave at 120° C. for 4 hours then forced air-cooled Purification by column chromatography [default gradient (ISCO); EtOAc/hexanes]

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a CEM snap top microwave vial (10 ml) equipped with a magnetic stir bar (3×10 mm) was added 5-Bromo-2-fluoroaniline (1.00 g, 5.26 mmol), sodium iodide (2.37 gm, 15.8 mmol), potassium carbonate (1.45 gm, 10.5 mmol), and 2-chloroethyl ether (1.30 gm, 9.09 mmol) in dimethylformamide (6.5 mL). The reaction was capped and irradiated in a CEM Explorer microwave at 120° C. for 4 hours then forced air-cooled. Purification by column chromatography [default gradient (ISCO); EtOAc/hexanes] afforded 397 mg (29%) an oil; 1H NMR (400 MHz, DMSO-d6) δ ppm 3.00 (t, J=1.7 Hz, 4H) 3.69-3.73 (m, 4H) 7.10-7.15 (m, 3H); MS (EI) m/z 259.0 [M+·]. To a CEM snap top microwave vial (10 ml) equipped with a magnetic stir bar (3×10 mm) The reaction was capped irradiated in a CEM Explorer microwave at 120° C. for 4 hours then forced air-cooled Purification by column chromatography [default gradient (ISCO); EtOAc/hexanes]