Water → 2,2'-(5-(8-(9-phenyl-9H-carbazol-3-yl)dibenzo[b,d]furan-2-yl)-1,3-phenylene)bis(benzo[d]oxazole)

HRID 1486381Notes

Reaction equation

HRID 1486381 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:15]=[CH:16][C:17]5[N:18]([C:27]6[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=6)[C:19]6[C:24]([C:25]=5[CH:26]=4)=[CH:23][CH:22]=[CH:21][CH:20]=6)=[CH:13][C:7]=3[C:6]=2[CH:33]=1.CC1(C)C(C)(C)OB([C:42]2[CH:43]=[C:44]([C:57]3[O:58][C:59]4[CH:65]=[CH:64][CH:63]=[CH:62][C:60]=4[N:61]=3)[CH:45]=[C:46]([C:48]3[O:49][C:50]4[CH:56]=[CH:55][CH:54]=[CH:53][C:51]=4[N:52]=3)[CH:47]=2)O1.C(=O)([O-])[O-].[K+].[K+].O1CCOCC1.[OH2:79]>[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:27]1([N:18]2[C:17]3[CH:16]=[CH:15][C:14]([C:12]4[CH:11]=[CH:10][C:8]5[O:79][C:5]6[CH:4]=[CH:3][C:2]([C:42]7[CH:47]=[C:46]([C:48]8[O:49][C:50]9[CH:56]=[CH:55][CH:54]=[CH:53][C:51]=9[N:52]=8)[CH:45]=[C:44]([C:57]8[O:58][C:59]9[CH:65]=[CH:64][CH:63]=[CH:62][C:60]=9[N:61]=8)[CH:43]=7)=[CH:33][C:6]=6[C:7]=5[CH:13]=4)=[CH:26][C:25]=3[C:24]3[C:19]2=[CH:20][CH:21]=[CH:22][CH:23]=3)[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

7

Reactant 5

HCID 962WaterHCID 11430Potassium CarbonateHCID 312751,4-DioxaneHCID 706610833-(8-bromodibenzo[b,d]furan-2-yl)-9-phenyl-9H-carbazoleHCID 867117283,5-Bis(benzo[d]oxazol-2-yl)phenylboronic Acid Pinacol Ester

Product 1

HCID 1176072612,2'-(5-(8-(9-phenyl-9H-carbazol-3-yl)dibenzo[b,d]furan-2-yl)-1,3-phenylene)bis(benzo[d]oxazole)

Reagents, catalysts & solvents 1

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalyst

Conditions

Temperature
100 °C

Procedure

A mixture of Compound 17 (1.25 g, 2.56 mmol), 2,2′-(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,3-phenylene)bis(benzo[d]oxazole) (1.23 g, 2.82 mmol), tetrakis(triphenylphosphine) palladium(0) (0.15 g, 0.13 mmol), potassium carbonate (1.06 g, 7.68 mmol), 1,4-dioxane (35.00 mL), and water (7.00 mL) was degassed with bubbling argon for 20 minutes. The reaction was then heated to 100° C. and stirred overnight (16.5 hours), maintaining an argon atmosphere. After adding water, the precipitated product was filtered, dried, washed with dichloromethane, and recrystallized from chloroform/acetone. The recrystallized product was collected to yield Host-11 (1.13 g, 61%). Confirmed by LCMS (APCI): calculated for C50H29N3O3 (M+H): 720. Found: 720.

Workup

  1. customwas degassed with bubbling argon for 20 minutes
  2. temperaturemaintaining an argon atmosphere
  3. additionAfter adding water
  4. filtrationthe precipitated product was filtered
  5. customdried
  6. washwashed with dichloromethane
  7. customrecrystallized from chloroform/acetone
  8. customThe recrystallized product was collected
  9. customto yield Host-11 (1.13 g, 61%)

Sources & evidence

ORD record
ord-f771c08009a246b48ddcef4a70b089fe
Source dataset
uspto-grants-2016_08
Patent number
US09425408B2

Reaction notes

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