반응 #57516

반응 방정식

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

3-methyl benzene boronic acid

potassium carbonate

→

solid

수율 63.0%

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

수율 63.0%

용매

N,N-dimethylformamide

반응 조건

후처리

1. 1
   기타The reaction mixture was degassed for 5 min
2. 2
   workup.STIRRINGby stirred at rt for 12 h
3. 3
   온도The mixture was cooled to room temperature
4. 4
   workup.ADDITIONthen poured into ethyl acetate (10 mL) and water (10 mL)
5. 5
   추출The aqueous layer was extracted with ethyl acetate (2×10 mL)
6. 6
   세척was washed by water (2×10 mL)
7. 7
   건조dried over Na2SO4
8. 8
   여과filtrated
9. 9
   기타evaporated in vacuo
10. 10
    기타The residue was purified by pre-HPLC

실험 절차

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).

출처