2,6-Lutidine → HCID 86718931, compound

Participants

Reaction Steps

To a solution of ethyl 4-(4-(tert-butoxycarbonyl)-2-((S)-3-((tert-butyldimethylsilyloxy)methyl)-1,2,3,4-tetrahydroisoquinoline-2-carbonyl)phenyl)-5-butyl-1-phenyl-1H-pyrazole-3-carboxylate (335 mg, 0.445 mmol) in THF (5.0 mL) was added 2,6-lutidine (0.10 mL, 0.89 mmol) followed by TMS-OTf (0.121 mL, 0.668 mmol). After stirring at room temperature for 1 h, the reaction mixture was heated at 50° C. for 1 h. Additional equivalents of both 2,6-lutidine and TMS-OTf were added hourly until consumption of the starting material (6 additions). After cooling to room temperature, the reaction mixture was quenched with sat. aq. sodium bicarbonate solution. The mixture was extracted with EtOAc concentrated in vacuo. The residue was purified by flash chromatography (Isco 40 g column eluting with 0-80% EtOAc/hexanes) to give the title compound (115 mg, 37%). MS(ESI+) m/z 696.3 (M+H)+.

Provenance & Evidence