Indole → N-(4-methylphenyl)indole

HRID 227857

반응식

HRID 227857 반응식
CC([O-])(C)C.[Na+].[NH:7]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH:9]=[CH:8]1.Br[C:17]1[CH:22]=[CH:21][C:20]([CH3:23])=[CH:19][CH:18]=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.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C1(C)C=CC=CC=1>[CH3:23][C:20]1[CH:21]=[CH:22][C:17]([N:7]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[CH:9]=[CH:8]2)=[CH:18][CH:19]=1

참가 물질

6

반응물 3

HCID 798IndoleHCID 78054-BromotolueneHCID 23676156Sodium t-butoxide

생성물 1

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

시약·촉매·용매 2

HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 1140Toluene용매

반응 조건

온도
100 °C

실험 절차

An oven-dried resealable Schlenk tube was purged with argon and charged with Pd2(dba)3 (11.2 mg, 0.012 mmol, 2.5 mol % Pd), 2 [Example 1] (14.4 mg, 0.036 mmol, 7.5 mol %), NaOt-Bu (130 mg, 1.35 mmol) and indole (115 mg, 0.98 mmol). The tube was purged with argon then toluene (1.0 mL) and 4-bromotoluene (120 μL, 0.98 mmol) were added through a rubber septum. The septum was removed, the tube was sealed with a teflon screw cap and the mixture was stirred at 100° C. for 21 h. The reaction was then diluted with ether (20 mL), filtered through celite and concentrated in vacuo. The crude material was purified by flash chromatography on silica gel to afford 191 mg (94%) of a colorless oil.

후처리

  1. customAn oven-dried resealable Schlenk tube was purged with argon
  2. customThe tube was purged with argon
  3. customThe septum was removed
  4. customthe tube was sealed with a teflon
  5. customscrew cap
  6. additionThe reaction was then diluted with ether (20 mL)
  7. filtrationfiltered through celite and
  8. concentrationconcentrated in vacuo
  9. customThe crude material was purified by flash chromatography on silica gel

출처 및 근거

ORD 기록
ord-5d4279b50360464c9a98c95f333ddb4e
출처 데이터셋
uspto-grants-2009_07
특허 번호
US07560582B2

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