Sodium t-butoxide → HCID 50939210, compound

Participants

Reaction Steps

Prepared according to procedure Y using 4-chloro-2-cyclopropyl-3-methyl-1,8-naphthyridine (40 mg, 0.183 mmol), 4-(3,3-dimethyl-2,3-dihydro-1H-pyrrolo[3,2-b]pyridin-6-yl)morpholine (42.7 mg, 0.183 mmol), XPhos precatalyst (13.52 mg, 0.018 mmol) and sodium tert-butoxide (35.2 mg, 0.366 mmol) by heating in toluene (4 mL) for 2 hours at 110° C. Purification by reverse phase HPLC (10 to 60% acetonitrile in water) gave 2-cyclopropyl-4-(3,3-dimethyl-6-(4-morpholinyl)-2,3-dihydro-1H-pyrrolo[3,2-b]pyridin-1-yl)-3-methyl-1,8-naphthyridine. 1H NMR (400 MHz, chloroform-d) δ ppm 8.98 (1H, dd, J=4.1, 2.0 Hz), 8.05 (1H, dd, J=8.2, 2.0 Hz), 7.59 (1H, d, J=2.3 Hz), 7.31 (1H, dd, J=8.3, 4.2 Hz), 5.69-5.74 (1H, m), 3.70-3.78 (6H, m), 2.90-3.03 (4H, m), 2.43-2.48 (3H, m), 2.30-2.40 (1H, m), 1.54-1.59 (4H, m), 1.45-1.53 (4H, m), 1.12-1.17 (2H, m). Mass Spectrum (ESI) m/e=416.2 (M+1).

Provenance & Evidence