Indole → N-(4-methylphenyl)indole

HRID 227857

反応式

HRID 227857 の反応式
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

参加物

6

反応物 3

HCID 798IndoleHCID 78054-BromotolueneHCID 23676156Sodium t-butoxide

生成物 1

HCID 9794286N-(4-methylphenyl)indole収率 94%

試薬・触媒・溶媒 2

HCID 9811564Bis(dibenzylideneacetone)palladium触媒HCID 1140Toluene溶媒

反応条件

温度
100 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-5d4279b50360464c9a98c95f333ddb4e
出典データセット
uspto-grants-2009_07
特許番号
US07560582B2

関連ノート

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