2-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenyl → 4-(3,3-dimethyl-6-(4-morpholinyl)-2,3-dihydro-1H-pyrrolo[3,2-b]pyridin-1-yl)-5,7-difluoro-3-methyl-2-(5-(methylsulfonyl)-3-pyridinyl)quinoline

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Reaction Steps

Prepared according to procedure Y by stirring 4-chloro-5,7-difluoro-3-methyl-2-(5-(methylsulfonyl)pyridin-3-yl)quinoline (40 mg, 0.108 mmol), 4-(3,3-dimethyl-2,3-dihydro-1H-pyrrolo[3,2-b]pyridin-6-yl)morpholine (25.3 mg, 0.108 mmol), Pd2dba3 (10.1 mg, 10.85 μmol), X-Phos (10.3 mg, 0.022 mmol), sodium tert-butoxide (31.3 mg, 0.325 mmol), and toluene (1.1 mL) at 105° C. for 30 min. Purification by reverse-phase HPLC (0-80% acetonitrile in water) gave 4-(3,3-dimethyl-6-(4-morpholinyl)-2,3-dihydro-1H-pyrrolo[3,2-b]pyridin-1-yl)-5,7-difluoro-3-methyl-2-(5-(methylsulfonyl)-3-pyridinyl)quinoline. 1H NMR (400 MHz, chloroform-d) δ ppm 9.28 (1H, d, J=2.2 Hz), 9.17-9.20 (1H, m), 8.56-8.59 (1H, m), 7.67-7.72 (1H, m), 7.58-7.61 (1H, m), 7.06-7.13 (1H, m), 5.79-5.82 (1H, m), 3.86-3.91 (1H, m), 3.74-3.81 (5H, m), 3.23 (3H, s), 3.02-3.08 (4H, m), 2.37-2.41 (3H, m), 1.65-1.74 (3H, m), 1.57-1.65 (3H, m). Mass Spectrum (ESI) m/e=566.2 (M+1).

Provenance & Evidence