Indole → N-(4-methylphenyl)indole

HRID 227862

반응식

HRID 227862 반응식
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.Cl[C:11]1[CH:16]=[CH:15][C:14]([CH3:17])=[CH:13][CH:12]=1.CC([O-])(C)C.[Na+]>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C1(P(C2CCCCC2)C2C=CC=CC=2C2C=CC=CC=2OC)CCCCC1.C1(C)C=CC=CC=1>[CH3:17][C:14]1[CH:15]=[CH:16][C:11]([N:1]2[C:9]3[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=3)[CH:3]=[CH:2]2)=[CH:12][CH:13]=1

참가 물질

7

반응물 3

HCID 798IndoleHCID 78104-ChlorotolueneHCID 23676156Sodium t-butoxide

생성물 1

HCID 9794286N-(4-methylphenyl)indole수율 94%

시약·촉매·용매 3

HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 117941862-(Dicyclohexylphosphino)-2'-methoxybiphenyl촉매HCID 1140Toluene용매

반응 조건

온도
100 °C

실험 절차

An oven-dried test tube was purged with argon and then charged with 2-dicyclohexylphosphino-2′-methoxy-1,1′-biphenyl (14.5 mg, 0.038 mmol, 7.5 mol %) and Pd2(dba)3 (11.6 mg, 0.013 mmol, 5.0 mol % Pd). Toluene (1.0 mL), indole (71 mg, 0.61 mmol), 4-chlorotoluene (60 mL, 0.51 mmol), and NaOt-Bu (70 mg, 0.73 mmol) were then added. The tube was fitted with a septum, purged with argon and heated at 100° C. for 28 h. The reaction was then cooled to room temperature, diluted with ether (20 mL), filtered through Celite and concentrated in vacuo. The residue was purified by flash chromatography on silica gel to afford 99 mg (94%) of a colorless oil.

후처리

  1. customAn oven-dried test tube was purged with argon
  2. customThe tube was fitted with a septum
  3. custompurged with argon
  4. temperatureThe reaction was then cooled to room temperature
  5. additiondiluted with ether (20 mL)
  6. filtrationfiltered through Celite
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by flash chromatography on silica gel

출처 및 근거

ORD 기록
ord-d9fb925b05a9485aa7060f8cf483127b
출처 데이터셋
uspto-grants-2009_07
특허 번호
US07560582B2

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