Reaction #74471

Reaction equation

N,N-dimethylformamide

compound 24

3-Chloro-6-(2-chloro-5-((2S,3S,4R,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)-tetrahydro-2H-pyran-2-yl)benzyl)pyridazine

→

title compound

Yield 52.0%

6-(2-Chloro-5-((2S,3S,4R,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)-tetrahydro-2H-pyran-2-yl)benzyl)pyridazine-3-carbonitrile

Yield 52.0%

Conditions

Workup

1. 1
   OtherThe capped reaction tube
2. 2
   Otherwas placed in a microwave reactor
3. 3
   Other(Biotage® Initiator™) and the mixture was irradiated at 160° C. for 15 min
4. 4
   WashAfter dilution with ethyl acetate, the organic layer was subsequently washed with water, 10 wt % potassium carbonate and brine
5. 5
   Dryingto drying over magnesium sulfate
6. 6
   FiltrationAfter filtration and concentration under reduced pressure
7. 7
   Otherthe residue was purified on a Biotage® purification apparatus (silica gel, 10 to 60% ethyl acetate in hexanes gradient)

Procedure

Intermediate 6 (compound 24, 4.0 g, 5.3 mmol) was added to a microwave reaction tube containing zinc cyanide (0.93 g, 7.9 mmol) and tetrakis(triphenylphosphine) palladium(0) (1.2 g, 1.1 mmol) in N,N-dimethylformamide (30 mL). The capped reaction tube was placed in a microwave reactor (Biotage® Initiator™) and the mixture was irradiated at 160° C. for 15 min. After dilution with ethyl acetate, the organic layer was subsequently washed with water, 10 wt % potassium carbonate and brine prior to drying over magnesium sulfate. After filtration and concentration under reduced pressure, the residue was purified on a Biotage® purification apparatus (silica gel, 10 to 60% ethyl acetate in hexanes gradient) to yield the title compound (2.0 g, 2.7 mmol, 52%) as a white solid.

Source