Реакция #57516

Уравнение реакции

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

3-methyl benzene boronic acid

potassium carbonate

→

solid

Выход 63.0%

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

Выход 63.0%

Растворители

N,N-dimethylformamide

Условия реакции

Обработка

1. 1
   ДругоеThe reaction mixture was degassed for 5 min
2. 2
   workup.STIRRINGby stirred at rt for 12 h
3. 3
   ТемператураThe mixture was cooled to room temperature
4. 4
   workup.ADDITIONthen poured into ethyl acetate (10 mL) and water (10 mL)
5. 5
   ЭкстракцияThe aqueous layer was extracted with ethyl acetate (2×10 mL)
6. 6
   Промывкаwas washed by water (2×10 mL)
7. 7
   Сушкаdried over Na2SO4
8. 8
   Фильтрацияfiltrated
9. 9
   Другоеevaporated in vacuo
10. 10
    ДругоеThe residue was purified by pre-HPLC

Методика

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).

Источник