Potassium Carbonate → 1,2-Diphenyl-1H-indole

HRID 48902

반응식

HRID 48902 반응식
[C:1]1([C:7]2[NH:8][C:9]3[C:14]([CH:15]=2)=[CH:13][CH:12]=[CH:11][CH:10]=3)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C([O-])([O-])=O.[K+].[K+].I[C:23]1[CH:28]=[CH:27][C:26](C)=[CH:25][CH:24]=1.C1OCCOCCOCCOCCOCCOC1>[Cu].ClC1C=CC=CC=1Cl>[C:23]1([N:8]2[C:9]3[C:14](=[CH:13][CH:12]=[CH:11][CH:10]=3)[CH:15]=[C:7]2[C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

참가 물질

7

반응물 4

HCID 11430Potassium CarbonateHCID 122074-IodotolueneHCID 136982-PhenylindoleHCID 2855718-Crown-6

생성물 1

HCID 876381,2-Diphenyl-1H-indole수율 75%

시약·촉매·용매 2

HCID 23978Copper촉매HCID 72391,2-Dichlorobenzene용매

반응 조건

온도
185 °C

실험 절차

A solution of dry o-dichlorobenzene containing 2-phenylindole (1 mmole) was added K2CO3 (1.5 mmole), 4-iodotoluene (1 mmole), copper powder (1.5 mmole) and 18-crown-6 (0.02 mmole), the reaction mixture was stirred under argon at 185° C. overnight. After cooling to room temperature, the reaction mixture was washed with hexane. The solid mixture was dissolved in EA, the K2CO3 and copper powder was removed by filtration. EA solution was evaporated under reduced pressure to give brown-red crude solid. Further purification by column chromatography on silica gel with hexane as an eluent gave a pale yellow solid of 1,2-diphenylindole (75% yield). The solid product (1 mmole) was dissolved in DMF (10 ml), a mixture of POCl3 (1.2 mmole) and DMF (1.2 mmole) was added dropwise. After stirring at 75° C. for 1 h, the reaction mixture was added into saturate NaHCO3 solution. The precipitated solid was collected by filtration and washed with ethanol to give a pale gray solid of 1,2-diphenylindole-3-carboxaldehyde (90% 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 1-4(32% yield). 1H-NMR (CDCl3, TMS) δ(ppm)=2.4 (s, 3H, Ar—CH3), 7.1-7.6, 8.2 (m, d, 17H, aromatic H).

후처리

  1. temperatureAfter cooling to room temperature
  2. washthe reaction mixture was washed with hexane
  3. dissolutionThe solid mixture was dissolved in EA
  4. customthe K2CO3 and copper powder was removed by filtration
  5. customEA solution was evaporated under reduced pressure
  6. customto give brown-red crude solid
  7. customFurther purification by column chromatography on silica gel with hexane as an eluent

출처 및 근거

ORD 기록
ord-2d4cc595b7284910a2feaefc3d5804ec
출처 데이터셋
uspto-grants-2004_03
특허 번호
US06706423B2

연결된 노트

불러오는 중…