Water → HCID 58431157, compound

Participants

Reaction Steps

To a solution of 6-[bis-(4-methoxy-benzyl)-amino]-pyridine-2-carbonitrile (1.83 g, 5.09 mmol) in anhydrous THF (64 mL) was added Ti(Oi-Pr)4 (1.79 mL, 6.11 mmol) in one portion followed by EtMgBr (3.0 M solution in THF, 4.07 mL, 12.2 mmol) slowly over 5 min. The reaction was stirred at room temperature overnight. Additional Ti(Oi-Pr)4 (0.5 mL, 1.7 mmol) and EtMgBr (1.2 mL, 3.60 mmol) were added and stirring was continued for 2 h. Additional Ti(Oi-Pr)4 (1.8 mL, 6.1 mmol) and EtMgBr (3 M, 4.1 mL, 12 mmol) were added and stirring was continued for 3 h. Water (12 mL) was added to the reaction mixture causing the formation of a precipitate. The mixture was filtered through a pad of diatomaceous earth and the filtrate was concentrated in vacuo to give an orange/red oil. The concentrate was re-dissolved in CH2Cl2, causing precipitation of a white solid. After filtration, the filtrate was concentrated in vacuo and purified via iterative flash chromatography on silica gel (1→10% MeOH/CH2Cl2) to give 381 mg of the title compound as a light orange viscous oil, m/z 391.08 [M+2]+.

Provenance & Evidence