Sodium Hydroxide → HCID 22561889, 화합물

HRID 982989노트

반응식

HRID 982989 반응식
Br[C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[CH:5][NH:6]2.[C:11]1([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:12](B(O)O)=[CH:13][CH:14]=[CH:15][CH:16]=1.[OH-].[Na+]>C1COCC1.[Pd].C(OCC)(=O)C>[C:11]1([C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH:12]=[CH:13][CH:14]=[CH:15][C:16]=1[C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[CH:5][NH:6]2

참가 물질

7

반응물 3

HCID 14798Sodium HydroxideHCID 6764944-BromoindoleHCID 4589187Biphenyl-2-boronic acid

생성물 1

HCID 22561889HCID 22561889, 화합물수율 93.6%

시약·촉매·용매 3

HCID 23938Palladium촉매HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

반응 조건

온도
75 °C

실험 절차

To a mixture of 4-bromoindole (1 g, 5 mmol), and 2-biphenylboronic acid (1 g, 5 mmol) in THF (17 mL) were added Palladium catalyst Pd(PPh3)4 (0.2 g, 0.17 mmol) and the freshly prepared sodium hydroxide solution (0.6 g, 15 mmol in 7 mL of water). The system was degassed and then charged with nitrogen. The degas procedure was repeated for three times. The mixture was stirred under nitrogen at 75° C. oil bath for overnight. TLC showed the completion of the coupling reaction. The mixture was cooled to room temperature, diluted with ethyl acetate, and separated from water layer. The ethyl acetate solution was washed with brine, and dried over Na2SO4. After filtration, the solvents were evaporated, and the crude product was purified on a silica gel column to give 1.26 g (93%) of 4-biphenyl-2-yl-1H-indole.

후처리

  1. customThe system was degassed
  2. additioncharged with nitrogen
  3. customthe completion of the coupling reaction
  4. temperatureThe mixture was cooled to room temperature
  5. customseparated from water layer
  6. washThe ethyl acetate solution was washed with brine
  7. dry with materialdried over Na2SO4
  8. filtrationAfter filtration
  9. customthe solvents were evaporated
  10. customthe crude product was purified on a silica gel column

출처 및 근거

ORD 기록
ord-1c1b3f51d80b4e19ae870d1323c661ef
출처 데이터셋
uspto-grants-2005_03
특허 번호
US06861418B2

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