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

HRID 1486380ノート

反応式

HRID 1486380 の反応式
[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

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 11979704Tetrakis(triphenylphosphine)palladium触媒HCID 962Water溶媒

反応条件

温度
80 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-e2c77f4bc16c48b99a9dd32cd7a8ae87
出典データセット
uspto-grants-2016_08
特許番号
US09425408B2

反応ノート

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