反応 #159449

反応方程式

3-(2,4-dioxobicyclo[3.2.1]oct-3-yl)-4-ethylphenylboronic acid

potassium phosphate

2-bromo-5-chloropyridine

tris(3-sulfophenyl)phosphine trisodium salt

→

3-[5-(5-chloropyridin-2-yl)-2-ethylphenyl]bicyclo[3.2.1]octane-2,4-dione

溶媒

water acetonitrile

反応条件

後処理

1. 1
   workup.ADDITIONis then added
2. 2
   その他by flushing with nitrogen
3. 3
   温度before heating at 160° C. under microwave irradiation for 15 minutes
4. 4
   温度After cooling to room temperature the reaction
5. 5
   その他is partitioned between 2M aqueous hydrochloric acid and dichloromethane
6. 6
   その他the organic phase is separated
7. 7
   抽出The aqueous phase is further extracted with dichloromethane
8. 8
   その他all organic fractions are combined then evaporated
9. 9
   その他The residue is purified by preparative reverse-phase HPLC

実験手順

To a microwave vial containing 3-(2,4-dioxobicyclo[3.2.1]oct-3-yl)-4-ethylphenylboronic acid (0.15 g, 0.52 mmol) and potassium phosphate (0.667 g, 3.15 mmol) is added 2-bromo-5-chloropyridine (0.121 g, 0.63 mmol), palladium acetate (4.0 mg, 0.016 mmol) and tris(3-sulfophenyl)phosphine trisodium salt (21 mg, 0.038 mmol). A degassed solvent mixture of water/acetonitrile (1.6 ml, 2:1 ratio) is then added, followed by flushing with nitrogen, then stirring at ambient temperature for 5 minutes before heating at 160° C. under microwave irradiation for 15 minutes. After cooling to room temperature the reaction is partitioned between 2M aqueous hydrochloric acid and dichloromethane, and the organic phase is separated. The aqueous phase is further extracted with dichloromethane and all organic fractions are combined then evaporated. The residue is purified by preparative reverse-phase HPLC to give 3-[5-(5-chloropyridin-2-yl)-2-ethylphenyl]bicyclo[3.2.1]octane-2,4-dione.

出典