Morpholine → 1'-[7-Fluoro-3-Methyl-2-(Pyridin-2-Yl)quinolin-4-Yl]-6'-(Morpholin-4-Yl)-1',2,2',3,5,6-Hexahydrospiro[pyran-4,3'-Pyrrolo[3,2-B]pyridine]

Participants

Reaction Conditions

Reaction Steps

Prepared according to procedure N using 6′-bromo-1′-(7-fluoro-3-methyl-2-(pyridin-2-yl)quinolin-4-yl)-1′,2,2′,3,5,6-hexahydrospiro[pyran-4,3′-pyrrolo[3,2-b]pyridine] (30 mg, 0.059 mmol), Pd2dba3 (5.4 mg, 5.94 μmol), morpholine (5.69 μL, 0.065 mmol), sodium tert-butoxide (11.4 mg, 0.119 mmol) and XPhos (5.66 mg, 0.012 mmol) in toluene (1.5 mL) and heating in the microwave for 1 h at 120° C. After purification 1′-(7-fluoro-3-methyl-2-(2-pyridinyl)-4-quinolinyl)-6′-(4-morpholinyl)-1′,2,2′,3,5,6-hexahydrospiro[pyran-4,3′-pyrrolo[3,2-b]pyridine] was obtained as a yellow film. 1H NMR (400 MHz, chloroform-d) δ ppm 8.75 (1H, dd, J=3.3, 1.0 Hz), 7.83-7.97 (3H, m), 7.75 (1H, dd, J=9.2, 6.1 Hz), 7.62 (1H, d, J=2.3 Hz), 7.41 (1H, ddd, J=7.0, 5.1, 2.0 Hz), 7.28-7.34 (1H, m), 5.83 (1H, d, J=2.3 Hz), 4.09-4.23 (2H, m), 3.95-4.04 (2H, m), 3.71-3.80 (4H, m), 3.52-3.62 (2H, m), 3.01 (4H, q, J=4.4 Hz), 2.32-2.46 (5H, m), 1.74-1.91 (2H, m). Mass Spectrum (ESI) m/e=512 (M+1).

Provenance & Evidence