Sodium t-butoxide → 4-(3,3-dimethyl-6-(4-morpholinyl)-2,3-dihydro-1H-pyrrolo[3,2-b]pyridin-1-yl)-2-(5-fluoro-3-pyridinyl)-3-methyl-1,7-naphthyridine

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Reaction Steps

Prepared according to procedure Y using 4-chloro-2-(5-fluoropyridin-3-yl)-3-methyl-1,7-naphthyridine (100 mg, 0.365 mmol), 4-(3,3-dimethyl-2,3-dihydro-1H-pyrrolo[3,2-b]pyridin-6-yl)morpholine (85 mg, 0.365 mmol), sodium tert-butoxide (70.2 mg, 0.731 mmol) and XPhos precatalyst (26.9 mg, 0.037 mmol) in toluene (4 mL) at 110° C. for 2 h. Purification by reverse phase HPLC (10 to 60% acetonitrile in water) gave 4-(3,3-dimethyl-6-(4-morpholinyl)-2,3-dihydro-1H-pyrrolo[3,2-b]pyridin-1-yl)-2-(5-fluoro-3-pyridinyl)-3-methyl-1,7-naphthyridine. 1H NMR (400 MHz, chloroform-d) δ ppm 9.52-9.64 (1H, m), 8.74 (1H, t, J=1.8 Hz), 8.63 (1H, d, J=2.7 Hz), 8.59 (1H, d, J=5.9 Hz), 7.76-7.82 (1H, m), 7.67 (1H, d, J=2.3 Hz), 7.55-7.59 (1H, m), 5.84 (1H, d, J=2.3 Hz), 3.81-3.93 (2H, m), 3.70-3.79 (4H, m), 2.95-3.07 (4H, m), 2.40 (3H, s), 1.60 (3H, s), 1.54 (3H, s). Mass Spectrum (ESI) m/e=471.2 (M+1).

Provenance & Evidence