Sodium t-butoxide → HCID 67285276, compound

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Reaction Steps

Prepared according to procedure Y using 4-chloro-3-methyl-2-phenyl-1,8-naphthyridine (60 mg, 0.236 mmol), 4-(3,3-dimethyl-2,3-dihydro-1H-pyrrolo[3,2-b]-pyridin-6-yl)morpholine (55 mg, 0.236 mmol), sodium tert-butoxide (45.3 mg, 0.471 mmol) and XPhos precatalyst (17.4 mg, 0.024 mmol). 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)-3-methyl-2-phenyl-1,8-naphthyridine. 1H NMR (400 MHz, chloroform-d) δ ppm 9.10 (1H, dd, J=4.1, 2.0 Hz), 8.16 (1H, dd, J=8.4, 2.0 Hz), 7.67-7.77 (2H, m), 7.62 (1H, d, J=2.3 Hz), 7.40-7.57 (4H, m), 5.80 (1H, d, J=2.3 Hz), 3.79-3.90 (2H, m), 3.70-3.77 (4H, m), 2.88-3.07 (4H, m), 2.36 (3H, s), 1.57 (3H, s), 1.52 (3H, s). Mass Spectrum (ESI) m/e=452.2 (M+1).

Provenance & Evidence