Trifluoroacetic acid → HCID 66604402, compound

Participants

Reaction Conditions

Reaction Steps

TFA (3 mL) was added to a mixture of methyl 7-((2S,6R)-2,6-dimethylmorpholino)-5-(4-methoxybenzyl)-2-(3-(trifluoromethyl)phenyl)-5H-pyrido[3,2-b]indole-4-carboxylate (27 mg, 0.045 mmol) and anisole (0.049 mL, 0.45 mmol) in a vial. The vial was sealed and heated at 60° C. for 3 hr and then 70° C. for an additional 4 hr. The solvent was removed and the residue was dissolved in EtOAc. This was washed with saturated aqueous NaHCO3 solution, brine, and then dried with sodium sulfate. Removal of the solvents followed by radial chromatography (step gradient elution with DCM containing 50 to 0% hexane followed by 10% EtOAc) to afforded methyl 7-((2S,6R)-2,6-dimethylmorpholino)-2-(3-(trifluoromethyl)phenyl)-5H-pyrido[3,2-b]indole-4-carboxylate (16 mg, 0.034 mmol, 75% yield) as a yellow oil. MS (ESI) m/z 484.1 (M+H). 1H NMR (400 MHz, chloroform-d) d ppm 9.41 (1H, s), 8.42 (1H, s), 8.32 (1H, d, J=7.30 Hz), 8.27 (1H, d, J=8.56 Hz), 8.16 (1H, s), 7.55-7.66 (2H, m), 7.00 (1H, dd, J=8.81, 2.01 Hz), 6.92 (1H, d, J=2.01 Hz), 4.08 (3H, s), 3.85 (2H, ddd, J=10.45, 6.30, 2.39 Hz), 3.63 (2H, d, J=10.58 Hz), 2.51-2.61 (2H, m), 1.30 (6H, d, J=6.04 Hz).

Provenance & Evidence