3,4-Dihydro-2H-1,4-benzoxazine → 4-(2H-benzo[b][1,4]oxazin-4(3H)-yl)-3-methoxybenzonitrile

Participants

Reaction Conditions

Reaction Steps

A mixture of 3,4-dihydro-2H-benzo[b][1,4]oxazine (500 mg, 3.69 mmol), 4-bromo-3-methoxybenzonitrile (784 mg, 3.69 mmol), Pd2(dba)3 (271 mg, 0.295 mmol), Xantphos (342 mg, 0.591 mmol) and sodium-tert-butoxide (590 mg, 6.14 mmol) in toluene (10 mL) was degassed for 10 minutes. The reaction mixture was heated at 100° C. for 1 h under microwave conditions. After completion, the reaction mixture was diluted with water (10 mL) and extracted with ethyl acetate (3×15 mL). The organic layer was dried over sodium sulfate and concentrated under reduced pressure to obtain the crude material which was purified by combi flash column chromatography (column size: 24 g; elution: 5% ethyl acetate in hexane) to obtain 4-(2H-benzo[b][1,4]oxazin-4(3H)-yl)-3-methoxybenzonitrile (790 mg, 80.2%) as yellow solid. m/z (ESI) 266.0 (M+H)+.

Provenance & Evidence