Potassium Carbonate → 3-(8-bromodibenzo[b,d]furan-2-yl)-9-phenyl-9H-carbazole

HRID 1486380

반응식

HRID 1486380 반응식
[C:1]1([N:7]2[C:19]3[CH:18]=[CH:17][C:16](B(O)O)=[CH:15][C:14]=3[C:13]3[C:8]2=[CH:9][CH:10]=[CH:11][CH:12]=3)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Br[C:24]1[CH:37]=[CH:36][C:27]2[O:28][C:29]3[CH:34]=[CH:33][C:32]([Br:35])=[CH:31][C:30]=3[C:26]=2[CH:25]=1.C(=O)([O-])[O-].[K+].[K+].O1CCOCC1>[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O>[Br:35][C:32]1[CH:33]=[CH:34][C:29]2[O:28][C:27]3[CH:36]=[CH:37][C:24]([C:16]4[CH:17]=[CH:18][C:19]5[N:7]([C:1]6[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=6)[C:8]6[C:13]([C:14]=5[CH:15]=4)=[CH:12][CH:11]=[CH:10][CH:9]=6)=[CH:25][C:26]=3[C:30]=2[CH:31]=1

참가 물질

7

반응물 4

HCID 11430Potassium CarbonateHCID 312751,4-DioxaneHCID 822902,8-DibromodibenzofuranHCID 513584509-Phenyl-9H-carbazole-3-boronic acid

생성물 1

HCID 706610833-(8-bromodibenzo[b,d]furan-2-yl)-9-phenyl-9H-carbazole수율 65%

시약·촉매·용매 2

HCID 11979704Tetrakis(triphenylphosphine)palladium촉매HCID 962Water용매

반응 조건

온도
80 °C

실험 절차

A mixture of (9-phenyl-9H-carbazol-3-yl)boronic acid (1.50 g, 5.22 mmol), 2,8-dibromodibenzo[b,d]furan (2.98 g, 9.14 mmol), tetrakis(triphenylphosphine) palladium(0) (0.30 g, 0.26 mmol), potassium carbonate (2.17 g, 15.67 mmol), 1,4-dioxane (50.00 mL), and water (10.00 mL) was degassed with bubbling argon for 30 min. The reaction mixture was then heated to 80° C. and was stirred overnight (16.5 hours), maintaining an argon atmosphere. Consumption of the starting material was confirmed by thin-layer chromatography and the reaction was cooled to room temperature. The product was extracted with dichloromethane, dried, and purified by silica gel column chromatography with dichloromethane in hexanes as the eluent. The product fractions were then dried and the product was collected to yield Compound 17 (1.65 g, 65%). Confirmed by LCMS (APCI): calculated for C30H18BrNO (M+H): 488. Found: 488.

후처리

  1. customwas degassed with bubbling argon for 30 min
  2. temperaturemaintaining an argon atmosphere
  3. customConsumption of the starting material
  4. temperaturethe reaction was cooled to room temperature
  5. extractionThe product was extracted with dichloromethane
  6. customdried
  7. custompurified by silica gel column chromatography with dichloromethane in hexanes as the eluent
  8. customThe product fractions were then dried
  9. customthe product was collected

출처 및 근거

ORD 기록
ord-e2c77f4bc16c48b99a9dd32cd7a8ae87
출처 데이터셋
uspto-grants-2016_08
특허 번호
US09425408B2

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