Reaction #8885

Reaction equation

triethylamine

product

[3-Amino-5-(4-chlorophenyl)-6-(2,4-dichlorophenyl)furo[2,3-b]pyridin-2-yl](pyridin-3-yl)methanone

trimethylacetyl chloride

→

title compound

N-[5-(4-Chlorophenyl)-6-(2,4-dichlorophenyl)-2-(pyridin-3-ylcarbonyl)furo[2,3-b]pyridin-3-yl]-2,2-dimethylpropanamide

Solvents

CH2Cl2

Conditions

Workup

1. 1
   workup.ADDITIONAfter the addition
2. 2
   OtherThe reaction was quenched with saturated NaHCO3 solution
3. 3
   OtherThe reaction mixture was partitioned between ethyl acetate and saturated NaHCO3 solution
4. 4
   WashThe organic layer was washed twice with saturated NaHCO3 solution, brine
5. 5
   Dryingdried (Na2SO4)
6. 6
   Filtrationfiltered
7. 7
   Concentrationconcentrated in vacuo
8. 8
   OtherPurification by MPLC (silica gel; 0% to 30% ethyl acetate:hexane gradient)

Procedure

A solution of 0.200 g (0.405 mmol) of the product from Example 26 in CH2Cl2 (4 mL) at 0° C. was treated with trimethylacetyl chloride (50 μL; 0.405 mmol) followed by triethylamine (113 μL; 0.810 mmol). After the addition, the reaction mixture was warmed to room temperature and stirred for 16 hours. The reaction was quenched with saturated NaHCO3 solution. The reaction mixture was partitioned between ethyl acetate and saturated NaHCO3 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 30% ethyl acetate:hexane gradient) gave the title compound. HPLC/MS: 578.0 (M+1), 580.0 (M+3); Rt=4.69 min.

Source