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

HRID 1486374Notes

Reaction equation

HRID 1486374 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]2[O:9][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]([N:50]3[C:62]4[CH:61]=[CH:60][CH:59]=[CH:58][C:57]=4[C:56]4[C:51]3=[CH:52][CH:53]=[CH:54][CH:55]=4)=CC=2)O1.C(=O)([O-])[O-].[K+].[K+].O1CCO[CH2:72][CH2:71]1>[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>[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:9][C:5]5[CH:4]=[CH:3][C:2]([C:59]6[CH:60]=[CH:61][C:62]([N:50]7[C:47]8[CH:48]=[CH:49][CH:44]=[CH:72][C:71]=8[C:56]8[C:51]7=[CH:52][CH:53]=[CH:54][CH:55]=8)=[CH:57][CH:58]=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 4

HCID 11430Potassium CarbonateHCID 312751,4-DioxaneHCID 118500739-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-9H-carbazoleHCID 1176072572-(4-(8-bromodibenzo[b,d]furan-2-yl)phenyl)-1-phenyl-1H-benzo[d]imidazole

Product 1

HCID 1176072459-(4-(8-(4-(1-phenyl-1H-benzo[d]imidazol-2-yl)phenyl)dibenzo[b,d]furan-2-yl)phenyl)-9H-carbazole

Reagents, catalysts & solvents 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of Compound 10 (1.25 g, 2.43 mmol), Compound 11 (0.931 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, dried, purified by silica gel column chromatography with acetone in hexanes as the eluent, and recrystallized from acetone/hexanes. The recrystallized product was collected to yield Host-5 (1.34 g, 82%). Confirmed by LCMS (APCI): calculated for C49H31N3O (M+H): 678. Found: 678.

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. customdried
  5. custompurified by silica gel column chromatography with acetone in hexanes as the eluent
  6. customrecrystallized from acetone/hexanes
  7. customThe recrystallized product was collected
  8. customto yield Host-5 (1.34 g, 82%)

Sources & evidence

ORD record
ord-b14ad53090d84cad8c71994d7b836b98
Source dataset
uspto-grants-2016_08
Patent number
US09425408B2

Reaction notes

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