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

Participants

Reaction Steps

Prepared according to procedure Y by using 4-chloro-3-methyl-2-(pyridin-2-yl)-1,8-naphthyridine (40 mg, 0.156 mmol), 4-(3,3-dimethyl-2,3-dihydro-1H-pyrrolo-[3,2-b]pyridin-6-yl)morpholine (36.5 mg, 0.156 mmol), XPhos precatalyst (11.5 mg, 0.015 mmol) and sodium tert-butoxide (30 mg, 0.313 mmol) in toluene (4 mL) for 2 h at 110° C. Purification by reverse phase HPLC (10 to 50% 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-(2-pyridinyl)-1,8-naphthyridine. 1H NMR (400 MHz, chloroform-d) δ ppm 9.12 (1H, dd, J=4.1, 2.0 Hz), 8.71 (1H, ddd, J=4.8, 1.9, 1.0 Hz), 8.14-8.21 (2H, m), 7.92 (1H, td, J=7.7, 1.8 Hz), 7.62 (1H, d, J=2.3 Hz), 7.37-7.48 (2H, m), 5.82 (1H, d, J=2.3 Hz), 3.86-3.91 (1H, m), 3.69-3.82 (5H, m), 2.93-3.04 (4H, m), 2.50 (3H, s), 1.58 (3H, s), 1.53 (3H, s). Mass Spectrum (ESI) m/e=453.2 (M+1).

Provenance & Evidence