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-(methylsulfonyl)phenyl)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)-7-fluoro-3-methyl-2-(2-(methylsulfonyl)phenyl)-quinoline (42 mg, 0.078 mmol) (described herein), morpholine (14 μL, 0.16 mmol), Pd2dba3 (5.0 mg, 5.4 μmol), 2-(dicyclohexylphosphino)-2,4,6-tri-1-propyl-1,1-biphenyl (5.6 mg, 0.012 mmol), and sodium tert-butoxide (15 mg, 0.155 mmol) in toluene (1.3 mL), and heating at 105° C. for 18 h. Purification afforded 4-(3,3-dimethyl-6-(4-morpholinyl)-2,3-dihydro-1H-pyrrolo[3,2-b]pyridin-1-yl)-7-fluoro-3-methyl-2-(2-(methylsulfonyl)phenyl)quinoline as a yellow powder. Compound is rotameric. 1H NMR (400 MHz, chloroform-d) δ ppm 8.15-8.29 (1H, m), 7.84-8.09 (1H, m), 7.77-7.83 (1H, m), 7.69-7.77 (2H, m), 7.55-7.69 (1H, m), 7.43-7.54 (1H, m), 7.31-7.43 (1H, m), 5.86 and 6.10 (1H, m), 4.05 (1H, m), 3.67-3.87 (5H, m), 3.14 (1H, m), 2.90-3.12 (6H, m), 2.00-2.16 (1H, m), 1.92 (2H, s), 1.46-1.68 (6H, m). Mass Spectrum (ESI) m/e=547 (M+1).

Provenance & Evidence