Morpholine → HCID 50938607, compound

Participants

Reaction Conditions

Reaction Steps

Prepared according to procedure N using 2-(3,5-bis(trifluoromethyl)phenyl)-5-fluoro-4-(6-iodo-3,3-dimethylindolin-1-yl)-3-methylquinoline (in a mixture with the 7-F regioisomer; described herein) (160 mg, 0.25 mmol), morpholine (43 μL, 0.50 mmol), Pd2dba3 (34.1 mg, 0.037 mmol), 2-(dicyclohexylphosphino)-2,4,6-tri-i-propyl-1,1-biphenyl (35.5 mg, 0.074 mmol), and sodium tert-butoxide (71.6 mg, 0.745 mmol) in toluene (2.5 mL). The reaction was stirred at 105° C. for 1 h. Purification afforded 2-(3,5-bis(trifluoromethyl)phenyl)-4-(3,3-dimethyl-6-(4-morpholinyl)-2,3-dihydro-1H-indol-1-yl)-5-fluoro-3-methylquinoline as a yellow oil. 1H NMR (400 MHz, chloroform-d) δ ppm 8.15 (2H, s), 8.00 (2H, t), 7.65 (1H, m), 7.28 (1H, m), 7.24 (1H, m), 7.17 (1H, m), 7.07 (1H, m), 3.62-3.95 (6H, m), 2.81-2.31 (4H, m), 2.35 (3H, s), 1.51 (3H, s), 1.45 (3H, s). Mass Spectrum (ESI) m/e=604 (M+1).

Provenance & Evidence