Morpholine → HCID 50939345, compound

Participants

Reaction Conditions

Reaction Steps

Prepared according to procedure N using 2-(3,5-bis(trifluoromethyl)phenyl)-7-fluoro-4-(6-iodo-3,3-dimethylindolin-1-yl)-3-methylquinoline (in a mixture with the 5-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)-7-fluoro-3-methylquinoline as a yellow oil. 1H NMR (400 MHz, chloroform-d) δ ppm 8.12 (2H, s), 8.00 (1H, s), 7.84-7.92 (1H, m), 7.80 (1H, ddd, J=9.5, 2.1, 1.0 Hz), 7.28-7.31 (1H, m), 7.10 (1H, dd, J=8.1, 1.1 Hz), 6.31-6.39 (1H, m), 5.57-5.64 (1H, m), 3.69-3.84 (6H, m), 2.93-3.00 (4H, m), 2.30 (3H, s), 1.53 (3H, s), 1.47 (3H, s). Mass Spectrum (ESI) m/e=604 (M+1).

Provenance & Evidence