Reaction #8902

Reaction equation

product

6-(2-Chlorophenyl)-5-(4-chlorophenyl)-2-oxo-1,2-dihydropyridine-3-carbonitrile

Cs2CO3

1-bromopinacolone

→

title compound

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

Solvents

DMF

ethyl acetate

Conditions

Workup

1. 1
   Washwashed with saturated NaCl/NaHCO3 solution (1:1)
2. 2
   OtherThe residue from the concentrated solution was purified via silica gel flash chromatography
3. 3
   Washeluting with a gradient of 0 to 75% ethyl acetate/hexane

Procedure

To a solution of 0.5 g (1.46 mmol) of the product of Step B in 10 mL DMF was added 0.954 g Cs2CO3 and 0.197 mL of 1-bromopinacolone. The reaction was stirred 17 hours at room temperature at which point the reaction mixture was diluted with ethyl acetate and washed with saturated NaCl/NaHCO3 solution (1:1). The residue from the concentrated solution was purified via silica gel flash chromatography eluting with a gradient of 0 to 75% ethyl acetate/hexane to afford the title compound. HPLC-MS: 439.1 (M+1), 441.1 (M+3); Rt=4.53 min.

Source