Sodium Carbonate → 2-Bromo-6-phenylpyridine

HRID 1183394Notes

Reaction equation

HRID 1183394 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Br:8])[N:3]=1.[C:9]1(B(O)O)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.C(=O)([O-])[O-].[Na+].[Na+]>CO.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>[Br:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[N:3]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 122742,6-DibromopyridineHCID 66827Phenylboronic Acid

Product 1

HCID 5686792-Bromo-6-phenylpyridine

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 887MethanolSolvent

Conditions

Temperature
100 °C

Procedure

2,6-Dibromo-pyridine (1.2 g, 0.508 mmol), phenylboronic acid (0.620 g, 0.508 mmol) and sodium carbonate (2 M aq., 30 mL) were dissolved in MeOH (10 mL) and toluene (30 mL) and the solution was degassed with bubbling N2 (g). Tetrakis(triphenylphosphine)palladium(0) (0.172 g, 0.149 mmol) was added and the reaction was heated to 100° C. overnight. After cooling the reaction was submitted to standard aqueous workup and purified by silica gel chromatography to give the title compound

Workup

  1. customtoluene (30 mL) and the solution was degassed with bubbling N2 (g)
  2. temperatureAfter cooling the reaction
  3. custompurified by silica gel chromatography

Sources & evidence

ORD record
ord-341f19c99b1346cf9fdcf3ccfb592a86
Source dataset
uspto-grants-2014_03
Patent number
US08664220B2

Reaction notes

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