2-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenyl → 4-(7-fluoro-3-methyl-2-(2-pyridinyl)-4-quinolinyl)-6-(4-morpholinyl)-3,4-dihydro-2H-1,4-benzoxazine

Participants

Reaction Steps

Prepared according to procedure Y by stirring 4-chloro-7-fluoro-3-methyl-2-(pyridin-2-yl)quinoline (50 mg, 0.183 mmol), 6-morpholino-3,4-dihydro-2H-benzo[b][1,4]oxazine (40.4 mg, 0.183 mmol), Pd2dba3 (16.8 mg, 0.018 mmol), XPhos (17.5 mg, 0.037 mmol) and sodium tert-butoxide (35.2 mg, 0.367 mmol) in toluene (2.0 mL) for 1 h at 120° C. in the microwave. Purification by reverse phase HPLC (10 to 60% acetonitrile in water) gave 4-(7-fluoro-3-methyl-2-(2-pyridinyl)-4-quinolinyl)-6-(4-morpholinyl)-3,4-dihydro-2H-1,4-benzoxazine). 1H NMR (400 MHz, chloroform-d) δ ppm 8.72-8.79 (1H, m), 7.81-7.96 (4H, m), 7.40 (1H, ddd, J=7.0, 5.0, 1.7 Hz), 7.28 (1H, ddd, J=9.2, 8.1, 2.6 Hz), 6.89 (1H, d, J=8.6 Hz), 6.29 (1H, dd, J=8.8, 2.7 Hz), 5.63 (1H, d, J=2.7 Hz), 4.40-4.51 (2H, m), 3.57-3.82 (6H, m), 2.71-2.82 (4H, m), 2.40 (3H, s). Mass Spectrum (ESI) m/e=457.0 (M+1).

Provenance & Evidence