Sodium hydride → 2-(2-Chloro-5-((2S,3S,4R,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)-tetrahydro-2H-pyran-2-yl)phenyl)(6-chloropyridazin-3-yl)methanone

Participants

Reaction Conditions

Reaction Steps

Sodium hydride (593 mg; 14.8 mmol; 60% in mineral oil) was added to stirred solution of Intermediate 1 (compound 6, 5.00 g; 7.42 mmol) in 20 mL of N,N-dimethylacetamide (DME) at 0° C. under nitrogen gas. The reaction mixture was stirred for 30 min, and 3,6-dichloropyridazine (compound 22, 1.25 g; 8.16 mmol) was added in one portion. The ice bath was removed, and the reaction mixture was stirred at room temperature for 3.5 h. Cooled to 0° C., H2O2 (2.50 mL) was added to reaction mixture and left stirring additional hour warm-up to room temperature. The reaction solution was washed with 1N HCl solution, 1N NaOH solution and brine. The organic layer was collected, and evaporated under a vacuum. The crude mixture was further purified by flash column chromatography (Biotage SP1™) to obtain 3.10 g (4.00 mmol; 54%) of the title compound as orange oil.

Provenance & Evidence