Morpholine → 4-(3,3-dimethyl-6-(4-morpholinyl)-2,3-dihydro-1H-pyrrolo[3,2-b]pyridin-1-yl)-5-fluoro-3-methyl-2-(2-pyridinyl)quinoline

Participants

Reaction Conditions

Reaction Steps

Prepared according to procedure N using 4-(6-bromo-3,3-dimethyl-2,3-dihydro-1H-pyrrolo[3,2-b]pyridin-1-yl)-5-fluoro-3-methyl-2-(pyridin-2-yl)quinoline (98.2 mg, 0.21 mmol) (described herein), morpholine (37 mg, 0.42 mmol), Pd2dba3 (29.1 mg, 0.032 mmol), 2-(dicyclohexylphosphino)-2,4,6-tri-i-propyl-1,1-biphenyl (30.3 mg, 0.064 mmol), and sodium tert-butoxide (50.9 mg, 0.53 mmol) in toluene (2.1 mL). The reaction mixture was stirred at 100° C. for 14 h. Purification afforded 4-(3,3-dimethyl-6-(4-morpholinyl)-2,3-dihydro-1H-pyrrolo[3,2-b]pyridin-1-yl)-5-fluoro-3-methyl-2-(2-pyridinyl)quinoline as a yellow solid. 1H NMR (400 MHz, chloroform-d) δ ppm 8.75 (1H, dt, J=4.8, 1.5 Hz), 8.03 (1H, dd, J=8.5, 1.3 Hz), 7.85-7.97 (2H, m), 7.58-7.68 (1H, m), 7.50-7.57 (1H, m), 7.36-7.45 (1H, m), 7.10-7.22 (1H, m), 5.70-5.80 (1H, m), 3.86 (1H, dd, J=8.8, 1.6 Hz), 3.66-3.78 (5H, m), 2.92-3.05 (4H, m), 2.40-2.50 (3H, m), 1.54-1.65 (3H, m), 1.45-1.54 (3H, m). Mass Spectrum (ESI) m/e=470 (M+1).

Provenance & Evidence