Dichloromethane → 4-Phenylpyridin-2-ol

HRID 1820695Notes

Reaction equation

HRID 1820695 reaction equation
[C:1]1(B(O)O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Br[C:11]1[CH:16]=[CH:15][N:14]=[C:13]([OH:17])[CH:12]=1.C(Cl)Cl>COCCOC.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:1]1([C:11]2[CH:16]=[CH:15][N:14]=[C:13]([OH:17])[CH:12]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 3

HCID 6344DichloromethaneHCID 66827Phenylboronic AcidHCID 178515446HCID 178515446, compound

Product 1

HCID 5987864-Phenylpyridin-2-olYield 64.1%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
90 °C

Procedure

Tetrakis(triphenylphosphine)palladium (0) (164 mg, 0.14 mmol) was added to a stirred suspension of phenylboronic acid (345 mg, 2.84 mmol) and 4-bromo-2-hydroxypyridine (494 mg, 2.84 mmol) in DME (10 mL). The reaction mixture was stirred under an argon atmosphere for 90 min. Degassed 2N potassium carbonate solution (aq) (10 mL) was added and the reaction mixture stirred with heating at 90° C. for 72 h. The solvent was evaporated in vacuo, and the residue partitioned between ethyl acetate and water. The aqueous layer was washed with ethyl acetate (×2). The organics were combined, dried over Na2SO4 and the solvent evaporated in vacuo. The residue was purified by chromatography on silica gel. Elution with DCM with a gradient to 5:95 methanol:DCM afforded 4-phenylpyridin-2-ol (311 mg, 1.82 mmol, 64%) M.S. (ESI) (m/z): 172 [M+H]+.

Workup

  1. customDegassed 2N potassium carbonate solution (aq) (10 mL)
  2. additionwas added
  3. stirringthe reaction mixture stirred
  4. customThe solvent was evaporated in vacuo
  5. customthe residue partitioned between ethyl acetate and water
  6. washThe aqueous layer was washed with ethyl acetate (×2)
  7. dry with materialdried over Na2SO4
  8. customthe solvent evaporated in vacuo
  9. customThe residue was purified by chromatography on silica gel
  10. washElution with DCM with a gradient to 5:95 methanol

Sources & evidence

ORD record
ord-43cdd6f3df0149068a07c703b511c076
Source dataset
uspto-grants-2009_10
Patent number
US07605170B2

Reaction notes

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