2-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenyl → HCID 50939861, compound

Participants

Reaction Steps

4-Chloro-5,7-difluoro-3-methyl-2-(1-phenylvinyl)quinoline (80 mg, 0.253 mmol), 4-(3,3-dimethyl-2,3-dihydro-1H-pyrrolo[3,2-b]pyridin-6-yl)morpholine (59.1 mg, 0.253 mmol), Pd2dba3 (23.2 mg, 0.025 mmol), 2-(dicyclohexylphosphino)-2′,4′,6′-tri-i-propyl-1,1′-biphenyl (24.2 mg, 0.051 mmol), sodium tert-butoxide (73.0 mg, 0.760 mmol), and toluene (2.53 mL) were stirred at 105° C. for 2 h. The reaction mixture was then concentrated and the resulting residue partitioned between EtOAc and saturated aqueous sodium bicarbonate solution. The organic layer was washed with brine and water, then dried (MgSO4) and concentrated. Purification by flash chromatography eluting with a gradient of 0-65% hexane in EtOAc gave 4-(3,3-dimethyl-6-(4-morpholinyl)-2,3-dihydro-1H-pyrrolo[3,2-b]pyridin-1-yl)-5,7-difluoro-3-methyl-2-(1-phenylethenyl)quinoline. 1H NMR (400 MHz, chloroform-d) δ ppm 7.72 (1H, m), 7.53 (1H, m), 7.28-7.33 (5H, m), 7.01 (1H, m), 6.02 (1H, d, J=0.8 Hz), 5.63 (1H, br. s.), 5.61 (1H, d, J=1.0 Hz), 3.87 (1H, m), 3.71-3.79 (4H, m), 3.61 (1H, m), 2.96 (4H, d, J=0.8 Hz), 2.02 (3H, s), 1.55 (6H, m). Mass Spectrum (ESI) m/e=513.2 (M+1).

Provenance & Evidence