Potassium Carbonate → HCID 117600334, compound

HRID 530415Notes

Reaction equation

HRID 530415 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([C:8]#[C:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:3]=1.[N:16]1[CH:21]=[CH:20][CH:19]=[C:18](B(O)O)[CH:17]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=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>[C:10]1([C:9]#[C:8][C:4]2[CH:3]=[C:2]([C:18]3[CH:17]=[N:16][CH:21]=[CH:20][CH:19]=3)[CH:7]=[CH:6][CH:5]=2)[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 27343783-Pyridinylboronic acidHCID 158361061-Bromo-3-(2-phenylethynyl)benzene

Product 1

HCID 117600334HCID 117600334, compoundYield 43.5%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

1-Bromo-3-(phenylethynyl)benzene (3 g, 11.7 mmol), 3-pyridylboronic acid (1.6 g, 13.0 mmol), Tetrakis(triphenylphosphine)palladium (0.3 g, 0.26 mmol) and potassium carbonate (3.2 g, 23.2 mmol) were dissolved in N,N-dimethylformamide and the reaction was stirred at 100° C. overnight under nitrogen. The mixture was extracted with dichloromethane and the combined organic phases were washed with water, dried over sodium sulfate and concentrated in vacuo to give the title compound as oil (1.3 g, 43% yield).

Workup

  1. extractionThe mixture was extracted with dichloromethane
  2. washthe combined organic phases were washed with water
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-fab913ab6e8649b28045d1acf3ce2b97
Source dataset
uspto-grants-2016_05
Patent number
US09353089B2

Reaction notes

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