Aniline → HCID 50991079, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 6-bromo-4-(5-chloro-2-methoxy-benzenesulfonyl)-3,4-dihydro-2H-benzo[1,4]oxazine-2-carboxylic acid ethyl ester (200 mg, 0.408 mmol), molybdenum hexacarbonyl (108 mg, 0.408 mmol), aniline (114 mg, 1.22 mmol), 1,8-diazabicyclo[5.4.0]undec-7-ene (192 mg, 1.22 mmol) trans-bis(μ-acetato)bis[o-(di-o-tolylphosphino)benzyl]dipalladium(II) (12 mg, 37 μmol), and tris(tert-butyl)phosphine tetrafluoroborate (6 mg, 20 μmol) in tetrahydrofuran (1 mL) was heated for 10 min at 140° C. under microwave irradiation, then the reaction mixture was partitioned between water and ethyl acetate. The organic layer was washed with brine, dried (MgSO4), and evaporated. Chromatography (SiO2, heptane-ethyl acetate gradient produced the title compound (111 mg, 51%). Off-white foam, MS (ISP)=531.0 (M+H)+.

Provenance & Evidence