Reaction #8882

Reaction equation

lithium bis(trimethylsilyl)amide

product

Ethyl {[5-(4-chlorophenyl)-3-cyano-6-(2,4-dichlorophenyl)pyridin-2-yl]oxy}acetate

→

title compound

Ethyl 3-amino-5-(4-chlorophenyl)-6-(2,4-dichlorophenyl)furo[2,3-b]pyridine-2-carboxylate

Solvents

THF

THF

Conditions

Workup

1. 1
   OtherThe reaction mixture was quenched at 0° C. with 10% aqueous NaHSO4 solution
2. 2
   OtherThe reaction mixture was partitioned between ethyl acetate and 10% NaHSO4 aqueous solution
3. 3
   WashThe organic layer was washed twice with saturated NaHCO3 solution, brine
4. 4
   Dryingdried (Na2SO4)
5. 5
   Filtrationfiltered
6. 6
   Concentrationconcentrated in vacuo
7. 7
   OtherPurification by MPLC (silica gel; 0% to 20% ethyl acetate:hexane gradient)

Procedure

A solution of the product from Step B (0.130 g; 0.282 mmol) in THF (3 mL) cooled to 0° C. was treated with 1 M solution of lithium bis(trimethylsilyl)amide in THF (0.85 mL; 0.85 mmol) and stirred at 0° C. under nitrogen for 30 minutes. The reaction mixture was quenched at 0° C. with 10% aqueous NaHSO4 solution. The reaction mixture was partitioned between ethyl acetate and 10% NaHSO4 aqueous solution. The organic layer was washed twice with saturated NaHCO3 solution, brine, dried (Na2SO4), filtered, and concentrated in vacuo. Purification by MPLC (silica gel; 0% to 20% ethyl acetate:hexane gradient) gave the title compound. HPLC/MS: 460.9 (M+1), 462.9 (M+3); Rt=4.35 min.

Source