Sodium t-butoxide → HCID 67284808, compound

Participants

Reaction Steps

Preparing according to procedure Y by using 4-(4-chloro-5,7-difluoro-3-methylquinolin-2-yl)-2,2-dimethylmorpholine (70.0 mg, 0.21 mmol), 4-(3,3-dimethyl-2,3-dihydro-1H-pyrrolo[3,2-b]pyridin-6-yl)morpholine (50 mg, 0.21 mmol), sodium tert-butoxide (20.60 mg, 0.21 mmol) and XPhos precatalyst (16 mg, 0.02 mmol) in toluene (4 mL) at reflux for 2 h. Purification by reverse phase HPLC (10 to 60% acetonitrile in water) gave 2-(2,2-dimethyl-4-morpholinyl)-4-(3,3-dimethyl-6-(4-morpholinyl)-2,3-dihydro-1H-pyrrolo[3,2-b]pyridin-1-yl)-5,7-difluoro-3-methylquinoline. 1H NMR (400 MHz, chloroform-d) δ ppm 7.56 (1H, d, J=2.3 Hz), 7.34-7.40 (1H, m), 6.69-6.82 (1H, m), 5.67 (1H, d, J=2.3 Hz), 3.90-4.02 (2H, m), 3.77-3.81 (1H, m), 3.71-3.76 (4H, m), 3.66 (1H, d, J=9.0 Hz), 3.27-3.37 (2H, m), 3.10-3.23 (2H, m), 2.92-3.01 (4H, m), 2.28 (3H, s), 1.53 (3H, d, J=0.8 Hz), 1.49 (3H, s), 1.40 (3H, s), 1.35 (3H, s). Mass Spectrum (ESI) m/e=524.2 (M+1).

Provenance & Evidence