Sodium Carbonate → 3-Bromo-5-(4-methoxyphenyl)pyridine

HRID 1878614Notes

Reaction equation

HRID 1878614 reaction equation
Br[C:2]1[CH:3]=[N:4][CH:5]=[C:6]([Br:8])[CH:7]=1.[CH3:9][O:10][C:11]1[CH:16]=[CH:15][C:14](B(O)O)=[CH:13][CH:12]=1.C([O-])([O-])=O.[Na+].[Na+]>CC#N.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:6]1[CH:5]=[N:4][CH:3]=[C:2]([C:14]2[CH:15]=[CH:16][C:11]([O:10][CH3:9])=[CH:12][CH:13]=2)[CH:7]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 693693,5-DibromopyridineHCID 201262(4-Methoxyphenyl)boronic acid

Product 1

HCID 120670673-Bromo-5-(4-methoxyphenyl)pyridine

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 6342AcetonitrileSolvent

Procedure

To a solution of 3,5-dibromopyridine (Sigma-Aldrich, St. Louis, USA) (1 eq, 8.4 mmol, 2 g) and 4-methoxy-phenylboronic acid (Sigma-Aldrich, St. Louis, USA) (1 eq, 8.4 mmol, 1.30 g) in MeCN (12 ml), Na2CO3 (2 eq, 16.7 mmol, 1.79 g) and Pd(PPh3)4 (0.04 eq, 0.334 mmol, 398 mg) are added. The mixture is heated using microwave radiation at 140° C. for 10 min. The solvents are evaporated, the residue is taken up in aqueous NaOH solution (1 M) and extracted with DCM. The organic layer is washed with brine, dried over MgSO4, filtered, and concentrated in vacuo. Purification by column chromatography (hexane/EtOAc) yields the title compound; [M+H]+=264/266.

Workup

  1. temperatureThe mixture is heated
  2. customat 140° C.
  3. customfor 10 min
  4. customThe solvents are evaporated
  5. extractionextracted with DCM
  6. washThe organic layer is washed with brine
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customPurification by column chromatography (hexane/EtOAc)

Sources & evidence

ORD record
ord-9851ea1746594511a32cc08516254079
Source dataset
uspto-grants-2012_11
Patent number
US08314112B2

Reaction notes

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