反応 #1952268

反応方程式

7-bromo-benzofuran

potassium acetate

bis(pinacolato)diboron

4-cyano-5-ethyl-1-methyl-3-(4-trifluoromethanesulfonyloxyphenyl)-1H-pyrrole-2-carboxylic acid ethyl ester

sodium carbonate water

→

title compound

収率 49.5%

3-(4-Benzofuran-7-yl-phenyl)-4-cyano-1-methyl-1H-pyrrole-2-carboxylic acid ethyl ester

収率 49.5%

溶媒

water

DMF

反応条件

後処理

1. 1
   その他while degassing with nitrogen
2. 2
   workup.STIRRINGAdd [11′bis(diphenylphosphino) ferrocene]dichloro-palladium(II) (30 mg) to the reaction mixture and stir at 80° C. for 2 hours under a nitrogen atmosphere
3. 3
   温度heat at 80° C. overnight
4. 4
   温度Cool to room temperature
5. 5
   抽出extract the desired product into ethyl acetate
6. 6
   洗浄Separate layers, and wash the organic layer once with water
7. 7
   乾燥dry over potassium carbonate
8. 8
   ろ過filter
9. 9
   濃縮concentrate under reduced vacuum
10. 10
    その他to give 1.08 g as a dark solid
11. 11
    その他Purify the material by silica gel chromatography (Chromatotron™)
12. 12
    洗浄eluting with hexane/ethyl acetate 7:3

実験手順

Add together 7-bromo-benzofuran (300 mg, 1.50 mmol), potassium acetate (431 mg, 2 Eq.), and bis(pinacolato)diboron (390 mg, 1.6 Eq.) in DMF (30 mL) and stir for 10 minutes while degassing with nitrogen. Add [11′bis(diphenylphosphino) ferrocene]dichloro-palladium(II) (30 mg) to the reaction mixture and stir at 80° C. for 2 hours under a nitrogen atmosphere. Cool mixture to room temperature and add 4-cyano-5-ethyl-1-methyl-3-(4-trifluoromethanesulfonyloxyphenyl)-1H-pyrrole-2-carboxylic acid ethyl ester (prepared in example E-97a or E-97b) (1.3 g, 2 Eq.), 2.0M sodium carbonate/water (3.6 mL ), and [11′bis(diphenylphosphino)ferrocene]dichloro-palladium(II) (30 mg) to the mixture and heat at 80° C. overnight. Cool to room temperature and pour into water and extract the desired product into ethyl acetate. Separate layers, and wash the organic layer once with water, dry over potassium carbonate, filter, and concentrate under reduced vacuum to give 1.08 g as a dark solid. Purify the material by silica gel chromatography (Chromatotron™) eluting with hexane/ethyl acetate 7:3 to provide 275 mg of the title compound as a white solid. Mass spectrum (m/e): 399.2 (M*+1).

出典