Indole → HCID 25051885, compound

Participants

Reaction Steps

Indole (20 mg, 0.17 mmol) was dissolved in DMF (400 μL) and NaH (60% dispersed in mineral oil, 9 mg, 0.22 mmol) was added and the resultant mixture was stirred at 60° C. for 30 minutes. The mixture was then cooled to room temperature to it was added crude chloride 2a (˜50 mg; excess). The reaction solution was then heated to 60° C. for 2 hours. The reaction solution was cooled to room temperature and diluted in EtOAc and the organic solution was washed with H2O (2×) and brine (1×). The organic layer was dried (MgSO4) and concentrated to provide crude 3a which was purified by preparative TLC (2:1:0.4 EtOAc/hexanes/Et3N) to give the desired product 3a (7 mg, 13% yield): LC-MS (Method B, retention time=0.448 min. MS calc'd for C19H28N3O (MH+): 314.2. Found 314.5.

Provenance & Evidence