Bromobenzene → 4-Phenyl-1H-indole

HRID 1839572ノート

反応式

HRID 1839572 の反応式
CC1(C)C(C)(C)OB([C:9]2[CH:17]=[CH:16][CH:15]=[C:14]3[C:10]=2[CH:11]=[CH:12][NH:13]3)O1.N1[C:27]2[CH:26]=[CH:25][CH:24]=[C:23](B([O-])[O-])[C:22]=2C=C1.BrC1C=CC=CC=1.[OH-].[Na+]>C1COCC1.[Pd]>[C:22]1([C:9]2[CH:17]=[CH:16][CH:15]=[C:14]3[C:10]=2[CH:11]=[CH:12][NH:13]3)[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1

参加物

7

反応物 4

HCID 7961BromobenzeneHCID 14798Sodium HydroxideHCID 113224711H-Indole-4-boronic acid, pinacol esterHCID 865876564-Indoleboronate

生成物 1

HCID 158062984-Phenyl-1H-indole収率 78%

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
70 °C

実験手順

To a mixture of 4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-indole (pinacole 4-indoleboronate (2 g, 8.2 mmol) and 3-bromobenzene (0.87 mL, 8.3 mmol) in THF (28 mL) were added Palladium catalyst Pd(PPh3)4 (284 mg, 0.25 mmol) and the freshly prepared sodium hydroxide solution (984 mg in 9 mL of water). The system was degassed and then charged with nitrogen for three times. The mixture was stirred under nitrogen at 70° C. oil bath for 6 hours. The reaction solution was cooled to room temperature, diluted with ethyl acetate and separated from water layer. The ethyl acetate solution was washed by brine, dried over Na2SO4 and concentrated. The residue was purified on a silica gel column eluting with hexanes:EtOAc 9:1 to give 1.38 g (78%) of 4-phenyl-1H-indole as a colorless liquid.

後処理

  1. customThe system was degassed
  2. additioncharged with nitrogen for three times
  3. temperatureThe reaction solution was cooled to room temperature
  4. additiondiluted with ethyl acetate
  5. customseparated from water layer
  6. washThe ethyl acetate solution was washed by brine
  7. dry with materialdried over Na2SO4
  8. concentrationconcentrated
  9. customThe residue was purified on a silica gel column
  10. washeluting with hexanes:EtOAc 9:1

出典と根拠

ORDレコード
ord-574e509badc846978c6ba6ef99fc3e23
出典データセット
uspto-grants-2004_01
特許番号
US06677368B2

反応ノート

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