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HRID 382064作成日:2026年10月27日

Sodium Carbonate → (z)-1,3-Dihydro-4-(6-indolyl)-3-[(3-methoxy-1h-pyrrol-2-yl)methylene]-2h-indol-2-one

https://huagongshe.com/reaction/382064

反応式

関与物質

役割名称HCID仕込み量
反応物Sodium CarbonateHCID 10340—
反応物1H-Indol-6-ylboronic acidHCID 2763205—
反応物(Z)-1,3-dihydro-4-iodo-3-[(3-methoxy-1H-pyrrol-2-yl)methylene]-2H-indol-2-oneHCID 15548053—
溶媒WaterHCID 962—
溶媒1,2-DimethoxyethaneHCID 8071—
生成物(z)-1,3-Dihydro-4-(6-indolyl)-3-[(3-methoxy-1h-pyrrol-2-yl)methylene]-2h-indol-2-oneHCID 984157062%

反応条件

温度90 °C

反応手順

A solution of 6-indoleboronic acid (36 mg, 0.22 mmol) (from Step A above), (Z)-1,3-dihydro-4-iodo-3-[(3-methoxy-1H-pyrrol-2-yl)methylene]-indol-2-one (54 mg, 0.15 mmol) (Starting Material 3) and sodium carbonate (52 mg, 0.49 mmol) in 5 mL DME and 2.5 mL water was degassed for 15 min. by bubbling argon through the solution. Dichlorobis(triphenylphosphine)palladium (II) (10 mol %) (Aldrich) was then added and the reaction was heated at 90° C. for 2 days. The reaction was then poured into 100 mL water and the product was extracted with ethyl acetate (4×50 mL). The combined organic layers were dried over magnesium sulfate and concentrated in vacuo. The resulting product, (Z)-1,3-dihydro-4-(6-indolyl)-3-[(3-methoxy-1H-pyrrol-2-yl)methylene]-2H-indol-2-one), was purified via flash column chromatography (40% EtOAc/hex) to yield 33 mg (62%) orange powder.

情報源と証拠

DOI10.6084/m9.figshare.5104873.v1
特許番号US06307056B1
出典データセットuspto-grants-2001_10
ORD IDord-35ebf44b134347d5b0c196889662e998
出典メモuspto-grants-2001_10