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HRID 61784作成日:2026年10月24日

Cesium carbonate → 9-(3-Hydroxy-3-methyl-but-1-ynyl)-8-methoxy-6,6-dimethyl-11-oxo-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrile

https://huagongshe.com/ja/reaction/61784

反応式

関与物質

役割名称HCID仕込み量
反応物Cesium carbonateHCID 10796—
反応物MethylbutynolHCID 148036—
反応物2-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylHCID 11155794—
反応物9-Bromo-8-methoxy-6,6-dimethyl-11-oxo-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrileHCID 54578544—
触媒Bis(acetonitrile)dichloropalladiumHCID 6093782—
溶媒WaterHCID 962—
溶媒AcetonitrileHCID 6342—
生成物9-(3-Hydroxy-3-methyl-but-1-ynyl)-8-methoxy-6,6-dimethyl-11-oxo-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrileHCID 66834347281.6%

反応条件

温度85 °C

反応手順

9-Bromo-8-methoxy-6,6-dimethyl-11-oxo-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrile (Compound E3-1-1, 50 mg, 0.13 mmol), bis(acetonitrile)dichloropalladium (II) (1.64 mg, 0.05 eq.), XPhos (9.05 mg, 0.15 eq.), cesium carbonate (185 mg, 4.5 eq.) and 3-methyl-1-butyn-1-ol (18.6 μl, 1.5 eq.) were dissolved in acetonitrile and stirred at 85° C. for 2 hr. The reaction solution was added to water, and then extracted with ethyl acetate. The organic layer was washed with brine and dried over sodium sulfate. The drying agent was removed by filtration and the residues obtained after concentration under reduced pressure were purified by HPLC to obtain the title compound (brown solid, 21.3 mg, 42%).

情報源と証拠

DOI10.6084/m9.figshare.5104873.v1
特許番号US09440922B2
出典データセットuspto-grants-2016_09
ORD IDord-0283fc9a817a4009991dc88d5add1d29
出典メモuspto-grants-2016_09