1-Iodo-2-(methoxymethoxy)benzene → 2-Benzyl-3-hydroxy-6-(2-hydroxyphenyl)pyridine

HRID 1359320Notes

Reaction equation

HRID 1359320 reaction equation
[CH2:1]([C:8]1[C:13]([O:14]COC)=[CH:12][CH:11]=[C:10]([Sn](CCCC)(CCCC)CCCC)[N:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.COC[O:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][C:36]=1I>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.C1(C)C(C)=CC=CC=1>[CH2:1]([C:8]1[C:13]([OH:14])=[CH:12][CH:11]=[C:10]([C:36]2[CH:37]=[CH:38][CH:39]=[CH:40][C:35]=2[OH:34])[N:9]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 117474651-Iodo-2-(methoxymethoxy)benzeneHCID 18182344HCID 18182344, compound

Product 1

HCID 1364432812-Benzyl-3-hydroxy-6-(2-hydroxyphenyl)pyridineYield 15.9%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 7237O-XyleneSolvent

Procedure

A mixture of 641 mg of (2-benzyl-3-methoxymethyloxy-6-pyridyl)tributyltin (Production Example 18), 327 mg of 2-methoxymethyloxyiodobenzene (Production Example 20), 71.6 mg of tetrakis(triphenylphosphine)palladium(0) and 7 ml of xylene was heated under refluxed for one hour in nitrogen atmosphere. After cooling as it was, the mixture was filtered through silica gel and the solvent was removed. To the residue was added 2 ml of trifluoroacetic acid, followed by stirring at room temperature overnight. The reaction solution was neutralized by aqueous potassium carbonate. Ethyl acetate was added thereto, and the organic phase was washed with water and brine, dried over anhydrous magnesium sulfate and the solvent was removed. The residue was subjected to silica gel column chromatography using 30% ethyl acetate/hexane, to give 54.5 mg of the target compound.

Workup

  1. temperaturewas heated
  2. temperatureunder refluxed for one hour in nitrogen atmosphere
  3. temperatureAfter cooling as it
  4. filtrationthe mixture was filtered through silica gel
  5. customthe solvent was removed
  6. additionTo the residue was added 2 ml of trifluoroacetic acid
  7. additionEthyl acetate was added
  8. washthe organic phase was washed with water and brine
  9. dry with materialdried over anhydrous magnesium sulfate
  10. customthe solvent was removed

Sources & evidence

ORD record
ord-47b586158c114d90a107136e0bafd536
Source dataset
uspto-grants-2003_07
Patent number
US06599917B1

Reaction notes

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