Methyl iodide → 1-Methyl-2-phenylindole

温度

65 °C

A solution of dry THF containing 2-phenylindole (1 mmole) was added NaH (1.1 mmole) and MeI (1.2 mmole, dropwise), and the reaction mixture was stirred at 65° C. for 3 h. After cooling to room temperature, the reaction mixture was poured into water and extracted with ether. The extracts was dried (MgSO4) and evaporated under reduced pressure to give yellow-orange solid. Further purification by column chromatography on silica gel with hexane as an eluent gave a pale yellow solid of 1-methyl-2-phenylindole (79% yield). The solid product (0.7 mmole) was dissolved in DMF (10 ml), a mixture of POCl3(0.09 mmole) and DMF (0.09 mmole) was added dropwise. After stirring at 75° C. for 1 h, the reaction mixture was added into saturate NaHCO3solution. The precipitated solid was collected by filtration and washed with ethanol to give a pale gray solid of 1-methyl-2-phenylindole-3-carboxaldehyde (85% yield). A dry DMF solution of the aldehyde (2 mmole) was added o-aminothiophenol (2.1 mmole) and Ac2O (0.5 ml) at room temperature. The mixture was stirred at 60° C. for 3 h. The reaction mixture was poured into stirred water and the precipitated solid was collected by filtration. The crude solid was washed with MeOH and recrystallized from benzene to afford compound 1-2 (38% yield). 1H-NMR (CDCl3, TMS) δ(ppm)=3.6 (s, 3H, —CH3), 7.3-7.8, 8.1, 8.9 (m, d, m, 13H, aromatic H).

1. temperatureAfter cooling to room temperature
2. extractionextracted with ether
3. dry with materialThe extracts was dried (MgSO4)
4. customevaporated under reduced pressure
5. customto give yellow-orange solid
6. customFurther purification by column chromatography on silica gel with hexane as an eluent

ORDレコード

ord-b45e070aca2446ab930ae18eee1dbc16

出典データセット

uspto-grants-2004_03

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US06706423B2