Water → HCID 56943928, compound

HRID 521555Notes

Reaction equation

HRID 521555 reaction equation
[C:1]1([N:7]2[C:19]3[CH:18]=[CH:17][C:16](B(O)O)=[CH:15][C:14]=3[C:13]3[C:8]2=[CH:9][CH:10]=[CH:11][CH:12]=3)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Br[C:24]1[N:29]=[CH:28][C:27]([C:30]2[CH:31]=[N:32][C:33](Br)=[CH:34][CH:35]=2)=[CH:26][CH:25]=1.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>[C:1]1([N:7]2[C:19]3[CH:18]=[CH:17][C:16]([C:24]4[N:29]=[CH:28][C:27]([C:30]5[CH:31]=[N:32][C:33]([C:16]6[CH:17]=[CH:18][C:19]7[N:7]([C:1]8[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=8)[C:8]8[C:13]([C:14]=7[CH:15]=6)=[CH:12][CH:11]=[CH:10][CH:9]=8)=[CH:34][CH:35]=5)=[CH:26][CH:25]=4)=[CH:15][C:14]=3[C:13]3[C:8]2=[CH:9][CH:10]=[CH:11][CH:12]=3)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

7

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 64263006,6'-Dibromo-3,3'-bipyridineHCID 513584509-Phenyl-9H-carbazole-3-boronic acid

Product 1

HCID 56943928HCID 56943928, compoundYield 64.2%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
85 °C

Procedure

A mixture of (9-phenyl-9H-carbazol-3-yl)boronic acid (1.41 g, 4.92 mmol), 6,6′-dibromo-3,3′-bipyridine (0.750 g, 2.39 mmol), tetrakis(triphenylphosphine)palladium(0) (0.166 g, 0.143 mmol), Na2CO3 (1.59 g, 15.0 mmol), H2O (15 mL) and THF (25 mL) was degassed with argon for about 25 min while stirring. The reaction mixture was then maintained at about 85° C. under argon. Upon confirming consumption of the starting material by thin layer chromatography (TLC) (SiO2, dichloromethane), the reaction was cooled to RT and poured over CH2Cl2 (ca. 350 mL). The organics were then washed with saturated NaHCO3, H2O and brine, dried over MgSO4, filtered and concentrated in vacuo. Purification of the crude via flash chromatography (SiO2, 100% CH2Cl2 to 29:1 CH2Cl2-acetone) afforded Compound 22 (0.98 g, 64%) as an off-white solid. MS (ES+) m/z: 639 (C46H30N4 requires 639).

Workup

  1. customwas degassed with argon for about 25 min
  2. customconsumption of the starting material by thin layer chromatography (TLC) (SiO2, dichloromethane)
  3. temperaturethe reaction was cooled to RT
  4. additionpoured over CH2Cl2 (ca. 350 mL)
  5. washThe organics were then washed with saturated NaHCO3, H2O and brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customPurification of the crude via flash chromatography (SiO2, 100% CH2Cl2 to 29:1 CH2Cl2-acetone)

Sources & evidence

ORD record
ord-31654eb5c7a4484880602cbfbbe8df0e
Source dataset
uspto-grants-2016_05
Patent number
US09328086B2

Reaction notes

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