Morpholine → 4-(3,3-Dimethyl-6-(4-morpholinyl)-2,3-dihydro-1H-pyrrolo[3,2-b]pyridin-1-yl)-7-fluoro-3-methyl-2-(2-pyridinyl)quinoline

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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)-7-fluoro-3-methyl-2-(pyridin-2-yl)quinoline (75 mg, 0.162 mmol), Pd2dba3 (3.8 mg, 0.016 mmol), XPhos (15.4 mg, 0.032 mmol), morpholine (1.6.9 mL, 0.194 mmol) and sodium tert-butoxide (31.1 mg, 0.324 mmol) in toluene (6 mL). After purification 4-(3,3-dimethyl-6-(4-morpholinyl)-2,3-dihydro-1H-pyrrolo[3,2-b]pyridin-1-yl)-7-fluoro-3-methyl-2-(2-pyridinyl)quinoline was obtained as a yellow solid. 1H NMR (400 MHz, chloroform-d) δ ppm 8.70-8.77 (1H, m), 7.75-7.96 (4H, m), 7.60 (1H, d, J=2.7 Hz), 7.41 (1H, ddd, J=7.1, 5.0, 1.6 Hz), 7.30 (1H, ddd, J=9.1, 8.1, 2.7 Hz), 5.83 (1H, d, J=2.3 Hz), 3.82 (2H, s), 3.69-3.77 (4H, m), 2.91-3.06 (4H, m), 2.38 (3H, s), 1.57-1.64 (3H, m), 1.50-1.56 (3H, m). Mass Spectrum (ESI) m/e=470 (M+1).

Provenance & Evidence