Indole → N-(4-methylphenyl)indole

HRID 1296995

反応式

HRID 1296995 の反応式
[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

参加物

7

反応物 3

HCID 798IndoleHCID 78104-ChlorotolueneHCID 23676156Sodium t-butoxide

生成物 1

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

試薬・触媒・溶媒 3

HCID 9811564Bis(dibenzylideneacetone)palladium触媒HCID 117941862-(Dicyclohexylphosphino)-2'-methoxybiphenyl触媒HCID 1140Toluene溶媒

反応条件

温度
100 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-64f2bd6e18764b81b7070c5cdc841e98
出典データセット
uspto-grants-2007_07
特許番号
US07247731B2

関連ノート

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