Réaction #57516

Équation de réaction

2-(2,4-Dichloro-benzoyl)-6-trifluoromethanesulfonyloxy-benzofuran-3-carboxylic acid ethyl ester

3-methyl benzene boronic acid

potassium carbonate

→

solid

Rendement 63.0%

2-(2,4-Dichloro-benzoyl)-6-m-tolyl-benzofuran-3-carboxylic acid ethyl ester

Rendement 63.0%

Solvants

N,N-dimethylformamide

Conditions de réaction

Traitement

1. 1
   AutreThe reaction mixture was degassed for 5 min
2. 2
   workup.STIRRINGby stirred at rt for 12 h
3. 3
   TempératureThe mixture was cooled to room temperature
4. 4
   workup.ADDITIONthen poured into ethyl acetate (10 mL) and water (10 mL)
5. 5
   ExtractionThe aqueous layer was extracted with ethyl acetate (2×10 mL)
6. 6
   Lavagewas washed by water (2×10 mL)
7. 7
   Séchagedried over Na2SO4
8. 8
   Filtrationfiltrated
9. 9
   Autreevaporated in vacuo
10. 10
    AutreThe residue was purified by pre-HPLC

Mode opératoire

To a solution of 2-(2,4-Dichloro-benzoyl)-6-trifluoromethanesulfonyloxy-benzofuran-3-carboxylic acid ethyl ester from step 4 (162 mg, 0.32 mmol, 1 eq) in anhydrous N,N-dimethylformamide (2 mL) were sequential added 3-methyl benzene boronic acid (64.6 mg, 0.63 mmol, 1.5 eq), potassium carbonate (87.6 mg, 0.63 mmol, 2 eq) and tetrakis(triphenylphosphine)palladium(0) (73.2 mg, 0.06 mmol, 0.2 eq) under argon. The reaction mixture was degassed for 5 min. The reaction was then stirred at 80° C. for 4 h followed by stirred at rt for 12 h. The mixture was cooled to room temperature then poured into ethyl acetate (10 mL) and water (10 mL). The aqueous layer was extracted with ethyl acetate (2×10 mL). Combined the organic layer was washed by water (2×10 mL), dried over Na2SO4, filtrated, and evaporated in vacuo. The residue was purified by pre-HPLC to afford an yellow solid (91.3 mg, 63%) as product. 1H-NMR (CDCl3): δ 8.04 (d, J=8.3 Hz, 1H), 7.73 (s, 1H), 7.64 (dd, J=1.5, 8.3 Hz, 1H), 7.57 (d, J=8.3 Hz, 1H), 7.47 (d, J=1.9 Hz, 1H), 7.41(m, 2H), 7.36(dd, J=1.9, 8.3 Hz, 1H), 7.34 (t, 1H), 7.19 (d, J=8.3 Hz, 1H), 4.245 (q, 2H), 2.43 (s, 3H), 1.28 (t, 3H); LC-MS (MH+=453/455).

Source