Potassium Carbonate → 2,2'-(5-(8-bromodibenzo[b,d]furan-2-yl)-1,3-phenylene)bis(1-phenyl-1H-benzo[d]imidazole)

HRID 1486378

反応式

HRID 1486378 の反応式
CC1(C)C(C)(C)OB([C:9]2[CH:10]=[C:11]([C:30]3[N:34]([C:35]4[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=4)[C:33]4[CH:41]=[CH:42][CH:43]=[CH:44][C:32]=4[N:31]=3)[CH:12]=[C:13]([C:15]3[N:19]([C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)[C:18]4[CH:26]=[CH:27][CH:28]=[CH:29][C:17]=4[N:16]=3)[CH:14]=2)O1.Br[C:47]1[CH:60]=[CH:59][C:50]2[O:51][C:52]3[CH:57]=[CH:56][C:55]([Br:58])=[CH:54][C:53]=3[C:49]=2[CH:48]=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:58][C:55]1[CH:56]=[CH:57][C:52]2[O:51][C:50]3[CH:59]=[CH:60][C:47]([C:9]4[CH:14]=[C:13]([C:15]5[N:19]([C:20]6[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=6)[C:18]6[CH:26]=[CH:27][CH:28]=[CH:29][C:17]=6[N:16]=5)[CH:12]=[C:11]([C:30]5[N:34]([C:35]6[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=6)[C:33]6[CH:41]=[CH:42][CH:43]=[CH:44][C:32]=6[N:31]=5)[CH:10]=4)=[CH:48][C:49]=3[C:53]=2[CH:54]=1

参加物

7

反応物 4

HCID 11430Potassium CarbonateHCID 312751,4-DioxaneHCID 822902,8-DibromodibenzofuranHCID 901995352,2'-(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,3-phenylene)bis(1-phenyl-1H-benzo[d]imidazole)

生成物 1

HCID 1176072502,2'-(5-(8-bromodibenzo[b,d]furan-2-yl)-1,3-phenylene)bis(1-phenyl-1H-benzo[d]imidazole)収率 56%

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 2,2′-(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,3-phenylene)bis(1-phenyl-1H-benzo[d]imidazole) (3.00 g, 5.10 mmol), 2,8-dibromodibenzo[b,d]furan (1.83 g, 5.61 mmol), tetrakis(triphenylphosphine) palladium(0) (0.30 g, 0.26 mmol), potassium carbonate (2.11 g, 15.30 mmol), 1,4-dioxane (90.00 mL), and water (18.00 mL) was degassed with bubbling argon for 50 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 ethyl acetate in dichloromethane as the eluent. The product fractions were then dried and the product was collected to yield Compound 14 (2.00 g, 56%). Confirmed by LCMS (APCI): calculated for C44H27BrN4O (M+H): 707. Found: 707.

後処理

  1. customwas degassed with bubbling argon for 50 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 ethyl acetate in dichloromethane 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-9f980e24c3f246619cfe71346ddc67d2
出典データセット
uspto-grants-2016_08
特許番号
US09425408B2

関連ノート

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