Water → 9-(4'-(8-(4-(1-phenyl-1H-benzo[d]imidazol-2-yl)phenyl)dibenzo[b,d]furan-2-yl)-[1,1'-biphenyl]-4-yl)-9H-carbazole

HRID 1486373Notes

Reaction equation

HRID 1486373 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]2O[C:8]3[CH:10]=[CH:11][C:12]([C:14]4[CH:19]=[CH:18][C:17]([C:20]5[N:24]([C:25]6[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=6)[C:23]6[CH:31]=[CH:32][CH:33]=[CH:34][C:22]=6[N:21]=5)=[CH:16][CH:15]=4)=[CH:13][C:7]=3[C:6]=2[CH:35]=1.CC1(C)C(C)(C)OB([C:44]2[CH:49]=[CH:48][C:47]([C:50]3[CH:55]=[CH:54][C:53]([N:56]4[C:68]5[CH:67]=[CH:66][CH:65]=[CH:64][C:63]=5[C:62]5[C:57]4=[CH:58][CH:59]=[CH:60][CH:61]=5)=[CH:52][CH:51]=3)=[CH:46][CH:45]=2)O1.C(=O)([O-])[O-].[K+].[K+].O1CCOCC1.[OH2:82]>[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>[C:25]1([N:24]2[C:23]3[CH:31]=[CH:32][CH:33]=[CH:34][C:22]=3[N:21]=[C:20]2[C:17]2[CH:18]=[CH:19][C:14]([C:12]3[CH:11]=[CH:10][C:8]4[O:82][C:5]5[CH:4]=[CH:3][C:2]([C:44]6[CH:49]=[CH:48][C:47]([C:50]7[CH:51]=[CH:52][C:53]([N:56]8[C:57]9[CH:58]=[CH:59][CH:60]=[CH:61][C:62]=9[C:63]9[C:68]8=[CH:67][CH:66]=[CH:65][CH:64]=9)=[CH:54][CH:55]=7)=[CH:46][CH:45]=6)=[CH:35][C:6]=5[C:7]=4[CH:13]=3)=[CH:15][CH:16]=2)[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1

Participants

7

Reactant 5

HCID 962WaterHCID 11430Potassium CarbonateHCID 312751,4-DioxaneHCID 582992689-(4'-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-[1,1'-biphenyl]-4-yl)-9H-carbazoleHCID 1176072572-(4-(8-bromodibenzo[b,d]furan-2-yl)phenyl)-1-phenyl-1H-benzo[d]imidazole

Product 1

HCID 1176072499-(4'-(8-(4-(1-phenyl-1H-benzo[d]imidazol-2-yl)phenyl)dibenzo[b,d]furan-2-yl)-[1,1'-biphenyl]-4-yl)-9H-carbazole

Reagents, catalysts & solvents 1

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalyst

Conditions

Temperature
100 °C

Procedure

A mixture of Compound 10 (1.25 g, 2.43 mmol), 9-(4′-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-[1,1′-biphenyl]-4-yl)-9H-carbazole (1.123 g, 2.52 mmol), tetrakis(triphenylphosphine) palladium(0) (0.14 g, 0.12 mmol), potassium carbonate (1.00 g, 7.27 mmol), 1,4-dioxane (25.00 mL), and water (5.00 mL) was degassed with bubbling argon for 45 minutes at 50° C. The reaction was then heated to 100° C. and stirred overnight (17 hours), maintaining an argon atmosphere. The precipitated product was filtered (filtrate saved for later purification), dried, and purified by column chromatography, on a silica gel column, with acetone in hexanes as the eluent. The product fractions were then dried to yield Host-4 (1.09 g). On the filtrate from the initial filtration, the material was extracted with ethyl acetate, dried, and purified by column chromatography, with the same eluent as the first column. The product fractions were then dried and combined with the collected product from the first column to yield a total of 1.40 g (76.2%) of Host-4. Confirmed by LCMS (APCI): calculated for C55H35N3O (M+H): 754. Found: 754.

Workup

  1. customwas degassed with bubbling argon for 45 minutes at 50° C
  2. temperaturemaintaining an argon atmosphere
  3. filtrationThe precipitated product was filtered
  4. custom(filtrate saved for later purification)
  5. customdried
  6. custompurified by column chromatography, on a silica gel column, with acetone in hexanes as the eluent
  7. customThe product fractions were then dried
  8. customto yield Host-4 (1.09 g)
  9. filtrationOn the filtrate from the initial filtration
  10. extractionthe material was extracted with ethyl acetate
  11. customdried
  12. custompurified by column chromatography, with the same eluent as the first column
  13. customThe product fractions were then dried
  14. customto yield a total of 1.40 g (76.2%) of Host-4

Sources & evidence

ORD record
ord-1cfd5512291648d4b3a3845631cf84f8
Source dataset
uspto-grants-2016_08
Patent number
US09425408B2

Reaction notes

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