反応 #159382

反応方程式

5-bromo-3-tert-butoxycarbonylaminothiophene-2-carboxylic acid methyl ester

2-bromo-5-fluoropyridine

bis(pinacolato)diboron

tri-t-butylphosphonium tetrafluoroborate

cesium carbonate

→

3-tert-Butoxycarbonylamino-5-(5-fluoropyridin-2-yl)thiophene-2-carboxylic acid methyl ester

溶媒

dioxane water

water

ethyl acetate

反応条件

後処理

1. 1
   抽出The aqueous phase was extracted several times with ethyl acetate
2. 2
   乾燥The combined organic phases were dried over sodium sulfate
3. 3
   濃縮concentrated
4. 4
   その他The crude product was purified by preparative HPLC
5. 5
   その他The product with the molecular weight of 352.39 (C16H17FN2O4S) was obtained in this way

実験手順

Palladium(II) acetate (20 mg) was added to a solution of 5-bromo-3-tert-butoxycarbonylaminothiophene-2-carboxylic acid methyl ester (300 mg), 2-bromo-5-fluoropyridine (235.5 mg), bis(pinacolato)diboron (462.2 mg), tri-t-butylphosphonium tetrafluoroborate (77.64 mg) and cesium carbonate (871.9 mg) in dioxane/water (6 mL/1.5 mL). The solution was heated at 90° C. for 3 h. The reaction solution was then mixed with ethyl acetate and water. The aqueous phase was extracted several times with ethyl acetate. The combined organic phases were dried over sodium sulfate and concentrated. The crude product was purified by preparative HPLC. The product with the molecular weight of 352.39 (C16H17FN2O4S) was obtained in this way; MS (ESI): 353 (M+H+).

出典