Trimethylaluminum → cis-5-Methoxy-1-[4-(1-methylpiperidin-4-yl)-1-naphthoyl]-6-(3,4,5-trimethylpiperazin-1-yl)indoline

Participants

Reaction Steps

A stirred solution of D3 (58 mg, 0.21 mmole) in toluene (5 ml) under argon was treated with 2M trimethylaluminium in toluene (0.13 ml, 0.25 mmole), then stirred at room temperature for 0.75 h. A solution of D9 (60 mg, 0.21 mmole) in toluene (5 ml) was added and the mixture was heated under reflux for 3.5 h, then allowed to cool to room temperature. The mixture was added to a 5 g silica gel column and eluted with 0-10% MeOH/DCM to afford a yellow oil. This was further purified by preparative plate TLC on silica gel eluting with 9:1:0.1 DCM/MeOH/0.88 NH3 to afford the title compound as a white solid (39 mg, 35%). MH+ 527.

Provenance & Evidence