Morpholine → HCID 50938606, compound

Participants

Reaction Conditions

Reaction Steps

Prepared according to procedure N using 5-chloro-2-(2-fluorophenyl)-4-(6-iodo-3,3-dimethylindolin-1-yl)-3-methylquinoline (14.4 mg, 0.027 mmol) (described herein), morpholine (5 μL, 0.05 mmol), Pd2dba3 (3.64 mg, 4.0 μmol), 2-(dicyclohexylphosphino)-2′,4′,6′-tri-i-propyl-1,1′-biphenyl (3.79 mg, 8.0 μmol), and sodium tert-butoxide (7.65 mg, 0.080 mmol) in toluene (1.0 mL). The reaction mixture was stirred at 100° C. for 1 h. Purification afforded 5-chloro-4-(3,3-dimethyl-6-(4-morpholinyl)-2,3-dihydro-1H-indol-1-yl)-2-(2-fluorophenyl)-3-methylquinoline as a yellow solid. 1H NMR (400 MHz, chloroform-d) δ ppm 8.12 (1H, dd, J=6.5, 3.1 Hz), 7.55-7.69 (3H, m), 7.41-7.52 (1H, m), 7.30-7.38 (1H, m), 7.14-7.23 (1H, m), 7.04 (1H, d, J=8.0 Hz), 6.25 (1H, d), 5.59 (1H, d), 3.98-4.08 (1H, m), 3.76 (4H, br. s.), 3.54 (1H, d, J=1.8 Hz), 3.01 (4H, br. s.), 2.12-2.25 (3H, m), 1.47-1.55 (3H, m), 1.42 (3H, s). Mass Spectrum (ESI) m/e=502 (M+1).

Provenance & Evidence