Sodium Carbonate → 3-(Pyridin-3-yl)phenol

HRID 558072Notes

Reaction equation

HRID 558072 reaction equation
Br[C:2]1[CH:3]=[N:4][CH:5]=[CH:6][CH:7]=1.C[O:9][C:10]1[CH:11]=[C:12](B(O)O)[CH:13]=[CH:14][CH:15]=1.C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1.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>[N:4]1[CH:5]=[CH:6][CH:7]=[C:2]([C:14]2[CH:15]=[C:10]([OH:9])[CH:11]=[CH:12][CH:13]=2)[CH:3]=1

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 122863-BromopyridineHCID 2734370(3-Methoxyphenyl)boronic acid

Product 1

HCID 129379483-(Pyridin-3-yl)phenol

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 3-bromopyridine, 3-methoxyphenylboronic acid (1.3 eq.), 2N sodium carbonate, and (PPh3)4Pd in toluene was stirred at 80° C. over night. The reaction mixture was taken up in ethyl acetate. The organic phase was washed with saturated sodium bicarbonate and then brine, dried, and concentrated. The residue was diluted in CDM and the solution was treated with boron tribromide at −78° C. (acetone-dry ice bath). The bath was allowed to warm up to room temperature over approximately 5 hr. Methanol was added to quench the reaction. The volatiles were removed under reduced pressure. The residue was taken up in ethyl acetate and the resultant solution was washed with saturated sodium bicarbonate. The organic phase was then extracted with 3 N hydrochloric acid, which was then basified with sodium bicarbonate The aqueous phase was extracted with ethyl acetate, which was washed with saturated brine, dried, and concentrated. The resultant white solid was pure by TLC, MS, and 1H-NMR and was used without further purification.

Workup

  1. washThe organic phase was washed with saturated sodium bicarbonate
  2. dry with materialbrine, dried
  3. concentrationconcentrated
  4. additionThe residue was diluted in CDM
  5. additionthe solution was treated with boron tribromide at −78° C. (acetone-dry ice bath)
  6. temperatureto warm up to room temperature over approximately 5 hr
  7. additionMethanol was added
  8. customto quench
  9. customthe reaction
  10. customThe volatiles were removed under reduced pressure
  11. washthe resultant solution was washed with saturated sodium bicarbonate
  12. extractionThe organic phase was then extracted with 3 N hydrochloric acid, which
  13. extractionwas extracted with ethyl acetate, which
  14. washwas washed with saturated brine
  15. customdried
  16. concentrationconcentrated
  17. custom1H-NMR and was used without further purification

Sources & evidence

ORD record
ord-424358f8bc604bca929da271958616a8
Source dataset
uspto-grants-2011_11
Patent number
US08063021B2

Reaction notes

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