Reaction #8894

Reaction equation

product

1-[3-Amino-5-(4-chlorophenyl)-6-(2,4-dichlorophenyl)furo[2,3-b]pyridin-2-yl]-2,2-dimethylpropan-1-one

4-chlorobutyryl chloride

triethylamine

→

title compound

4-Chloro-N-[5-(4-chlorophenyl)-6-(2,4-dichlorophenyl)-2-(2,2-dimethylpropanoyl)furo[2,3-b]pyridin-3-yl]butanamide

Solvents

CH2Cl2

Conditions

Workup

1. 1
   OtherThe reaction mixture was then partitioned between saturated aqueous NaHCO3 and EtOAc
2. 2
   OtherThe organic layer was separated
3. 3
   Washwashed with aq. NaHCO3, brine
4. 4
   Dryingdried (Na2SO4)
5. 5
   Filtrationfiltered
6. 6
   Otherevaporated
7. 7
   OtherThe residue was purified on a silica gel flash chromatography column
8. 8
   Washeluted with 0–20% EtOAc-hexane
9. 9
   OtherEvaporation of the purified fractions
10. 10
    Otherdrying in vacuo

Procedure

To a magnetically stirred solution of 0.300 g (0.63 mmol) of the product of Example 17 in 6 mL of CH2Cl2 at 0° C. was added 70 μL (0.63 mmol) of 4-chlorobutyryl chloride and 96 mg (0.95 mmol) of triethylamine. The reaction was stirred for 1.5 h and allowed to warm to room temperature. The reaction mixture was then partitioned between saturated aqueous NaHCO3 and EtOAc. The organic layer was separated, washed with aq. NaHCO3, brine, then dried (Na2SO4), filtered and evaporated. The residue was purified on a silica gel flash chromatography column eluted with 0–20% EtOAc-hexane. Evaporation of the purified fractions and drying in vacuo afforded the title compound. HPLC/MS: 577.0 (M+1), 578.9 (M+3); Rt=5.05 min.

Source