Toluene → HCID 66880499, compound

HRID 1893546Notes

Reaction equation

HRID 1893546 reaction equation
C1(C)C=CC=CC=1.[CH3:8][C:9]1[CH:14]=[CH:13][C:12](B(O)O)=[CH:11][C:10]=1[N+:18]([O-:20])=[O:19].Br[C:22]1[N:27]=[CH:26][CH:25]=[CH:24][N:23]=1.C(=O)([O-])[O-].[Na+].[Na+]>C(OCC)(=O)C.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(O)C>[CH3:8][C:9]1[CH:14]=[CH:13][C:12]([C:22]2[N:27]=[CH:26][CH:25]=[CH:24][N:23]=2)=[CH:11][C:10]=1[N+:18]([O-:20])=[O:19]

Participants

8

Reactant 4

HCID 1140TolueneHCID 10340Sodium CarbonateHCID 783452-BromopyrimidineHCID 27735154-Methyl-3-nitrobenzeneboronic acid

Product 1

HCID 66880499HCID 66880499, compoundYield 55%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a toluene (40 ml)-ethanol (40 ml) mixed solvent were added 4-methyl-3-nitrophenylboronic acid (2.66 g, 14.7 mmol), 2-bromopyrimidine (3.15 g, 19.81 mmol), tetrakis(triphenylphosphine)palladium(0) (1.01 g, 0.874 mmol) and sodium carbonate (3.93 g, 37.08 mmol), and the mixture was heated under reflux for 24 hr. The reaction mixture was cooled, diluted with ethyl acetate, washed with diluted aqueous sodium hydroxide solution and saturated brine, and dried over anhydrous magnesium sulfate. The insoluble material was filtered off, and the solution was concentrated under reduced pressure to give a solid. This was purified by silica gel column chromatography (ethyl acetate-dichloromethane) to give the title compound (1.74 g, yield 55%) as a colorless solid.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 24 hr
  3. temperatureThe reaction mixture was cooled
  4. washwashed with diluted aqueous sodium hydroxide solution and saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationThe insoluble material was filtered off
  7. concentrationthe solution was concentrated under reduced pressure
  8. customto give a solid
  9. customThis was purified by silica gel column chromatography (ethyl acetate-dichloromethane)

Sources & evidence

ORD record
ord-a8b7acfd0eb24647bc6372ea3ac715c6
Source dataset
uspto-grants-2013_08
Patent number
US08513235B2

Reaction notes

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