2-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenyl → 4-(3,3-dimethyl-6-(4-morpholinyl)-2,3-dihydro-1H-pyrrolo[3,2-b]pyridin-1-yl)-3-methyl-2-(4-methyl-2-pyridinyl)-1,8-naphthyridine

Participants

Reaction Steps

Prepared according to procedure Y using 4-(3,3-dimethyl-2,3-dihydro-1H-pyrrolo[3,2-b]pyridin-6-yl)morpholine (18 mg, 0.077 mmol), 4-chloro-3-methyl-2-(4-methylpyridin-2-yl)-1,8-naphthyridine (20.81 mg, 0.077 mmol), sodium tert-butoxide (14.86 mg, 0.154 mmol) and XPhos (7.72 mmol, 7.72 mol) 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)-3-methyl-2-(4-methyl-2-pyridinyl)-1,8-naphthyridine. 1H NMR (400 MHz, chloroform-d) δ ppm 9.12 (1H, dd, J=4.3, 2.0 Hz), 8.57 (1H, d, J=5.1 Hz), 8.17 (1H, dd, J=8.2, 2.0 Hz), 8.00-8.03 (1H, m), 7.61 (1H, d, J=2.3 Hz), 7.44 (1H, dd, J=8.3, 4.2 Hz), 7.22 (1H, ddd, J=5.1, 1.8, 0.8 Hz), 5.81 (1H, d, J=2.3 Hz), 3.86-3.90 (1H, m), 3.77-3.82 (1H, m), 3.72-3.77 (4H, m), 2.93-3.04 (4H, m), 2.50 (3H, s), 2.49 (3H, s), 1.58 (3H, s), 1.53 (3H, s). Mass Spectrum (ESI) m/e=467.2 (M+1).

Provenance & Evidence