Sodium t-butoxide → 4-(3,3-dimethyl-6-(4-morpholinyl)-2,3-dihydro-1H-pyrrolo[3,2-b]pyridin-1-yl)-2-(3-fluorophenyl)-3-methyl-1,8-naphthyridine

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Reaction Steps

Prepared according to procedure Y using 4-chloro-2-(3-fluorophenyl)-3-methyl-1,8-naphthyridine (70.1 mg, 0.257 mmol), 4-(3,3-dimethyl-2,3-dihydro-1H-pyrrolo[3,2-b]pyridin-6-yl)morpholine (60 mg, 0.257 mmol), sodium tert-butoxide (49.4 mg, 0.514 mmol) and XPhos precatalyst (18.9 mg, 0.026 mmol) in toluene (4 mL) for 2 hours at 110° C. 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-(3-fluorophenyl)-3-methyl-1,8-naphthyridine. 1H NMR (400 MHz, chloroform-d) δ ppm 9.12 (1H, dd, J=4.3, 2.0 Hz), 8.17 (1H, dd, J=8.4, 2.0 Hz), 7.64 (1H, d, J=2.3 Hz), 7.42-7.54 (4H, m), 7.13-7.23 (1H, m), 5.79 (1H, d, J=2.3 Hz), 3.86-3.91 (1H, m), 3.80-3.84 (1H, m), 3.72-3.79 (4H, m), 2.94-3.05 (4H, m), 2.37 (3H, s), 1.58 (3H, s), 1.53 (3H, s). Mass Spectrum (ESI) m/e=470.2 (M+1)

Provenance & Evidence