N,N'-Dimethylethylenediamine → HCID 69058741, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of (±)-cis-tert-butyl 5-oxo-6-(trifluoromethyl)-3,3a,4,5-tetrahydro-1H-pyrrolo[3,4-c]isoquinoline-2(9bH)-carboxylate from Example 1, Part H (50 mg, 0.14 mmol) in 4 mL of toluene in a screw-cap vial was added copper (I) iodide (2.6 mg, 0.014 mmol) and potassium phosphate (65 mg, 0.31 mmol). The reaction was degassed with a stream of argon for several minutes, and then there was added iodobenzene (17 μL, 0.154 mmol) and N,N′-dimethylethylenediamine (3.0 μL, 0.028 mmol). The reaction was allowed to stir at 90° C. in the sealed vial for 18 h. The reaction was quenched with water, diluted with EtOAc and washed with 1N HCl, sat'd aq NaHCO3 and brine, dried (MgSO4) and concentrated in vacuo. The residue was purified by flash chromatography (230-400 mesh silica gel, elution with 2:1 hexane/EtOAc) to afford 48 mg (80%) of the title compound. LRMS (ESI): 377.23 (M+H—C4H8)+.

Provenance & Evidence