Water → 6,6'-bis(4-(9H-carbazol-9-yl)phenyl)-3,3'-bipyridine

HRID 521544Notes

Reaction equation

HRID 521544 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:13]=[CH:12][C:11]([N:14]3[C:26]4[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=4[C:20]4[C:15]3=[CH:16][CH:17]=[CH:18][CH:19]=4)=[CH:10][CH:9]=2)=[N:6][CH:7]=1.CC1(C)C(C)(C)OB(C2C=CC([C:41]3[CH:46]=[CH:45][C:44]([N:47]4[C:59]5[CH:58]=CC=C[C:54]=5C5C4=CC=CC=5)=[CH:43][CH:42]=3)=NC=2)O1.C([O-])([O-])=O.[Na+].[Na+].O>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1COCC1>[CH:25]1[C:26]2[N:14]([C:11]3[CH:12]=[CH:13][C:8]([C:5]4[N:6]=[CH:7][C:2]([C:2]5[CH:7]=[N:6][C:5]([C:8]6[CH:13]=[CH:54][C:59]([N:47]7[C:44]8[CH:45]=[CH:46][CH:41]=[CH:42][C:43]=8[C:15]8[C:20]7=[CH:19][CH:18]=[CH:17][CH:16]=8)=[CH:58][CH:9]=6)=[CH:4][CH:3]=5)=[CH:3][CH:4]=4)=[CH:9][CH:10]=3)[C:15]3[C:20](=[CH:19][CH:18]=[CH:17][CH:16]=3)[C:21]=2[CH:22]=[CH:23][CH:24]=1

Participants

7

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 667995889-(4-(5-bromopyridin-2-yl)phenyl)-9H-carbazoleHCID 668014339-(4-(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl)phenyl)-9H-carbazole

Product 1

HCID 569437306,6'-bis(4-(9H-carbazol-9-yl)phenyl)-3,3'-bipyridineYield 180%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 6 (4.11 g, 10.3 mmol), 7 (4.60 g, 10.3 mmol), tetrakis(triphenylphosphine)palladium(0) (0.595 g, 0.515 mmol), Na2CO3 (5.41 g, 51.0 mmol), H2O (55 mL) and THF (92 mL) was degassed with argon for about 1 h while stirring. The stirring reaction mixture was then maintained under argon at about 80° C. for about 18 h. Upon confirming consumption of the starting materials by TLC (SiO2, 49:1 dichloromethane-acetone), the reaction was cooled to RT, filtered and filtrant washed with EtOAc and H2O to afford 8 (5.92 g, 90%) as an off-white solid.

Workup

  1. customwas degassed with argon for about 1 h
  2. customThe stirring reaction mixture
  3. customconsumption of the starting materials by TLC (SiO2, 49:1 dichloromethane-acetone)
  4. temperaturethe reaction was cooled to RT
  5. filtrationfiltered
  6. washfiltrant washed with EtOAc and H2O

Sources & evidence

ORD record
ord-4a6c1509b92a434e8df8481f6a34bfe6
Source dataset
uspto-grants-2016_05
Patent number
US09328086B2

Reaction notes

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