Bromobenzene → 4-Phenyl-1H-indole

HRID 982975노트

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HRID 982975 반응식
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

참가 물질

7

반응물 4

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

생성물 1

HCID 158062984-Phenyl-1H-indole수율 78%

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 8028Tetrahydrofuran용매

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온도
70 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-7868c3ce25084aeaacfcf29dbb412fc8
출처 데이터셋
uspto-grants-2005_03
특허 번호
US06861418B2

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