5-Methyl-2-(tri-n-butylstannyl)pyridine → Methyl 3-hydroxy-5-(5-methylpyridin-2-yl)benzoate

HRID 1845285Notes

Reaction equation

HRID 1845285 reaction equation
[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[C:8]([OH:10])[CH:7]=[C:6](Br)[CH:5]=1.[CH3:13][C:14]1[CH:15]=[CH:16][C:17]([Sn](CCCC)(CCCC)CCCC)=[N:18][CH:19]=1>C1(C)C=CC=CC=1.CN(C=O)C.O.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[OH:10][C:8]1[CH:9]=[C:4]([CH:5]=[C:6]([C:17]2[CH:16]=[CH:15][C:14]([CH3:13])=[CH:19][N:18]=2)[CH:7]=1)[C:3]([O:2][CH3:1])=[O:12]

Participants

7

Reactant 2

HCID 111327115-Methyl-2-(tri-n-butylstannyl)pyridineHCID 53216607Methyl 3-bromo-5-hydroxybenzoate

Product 1

HCID 58188160Methyl 3-hydroxy-5-(5-methylpyridin-2-yl)benzoate

Reagents, catalysts & solvents 4

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 962WaterSolventHCID 1140TolueneSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 3-bromo-5-hydroxy-benzoic acid methyl ester (1.47 g, 6.36 mmol), 5-methyl-2-(tributylstannyl)pyridine (3.0 g, 7.85 mmol), tetrakis(triphenylphosphine)-palladium(0) (300 mg, 0.26 mmol) in toluene (20 mL) and DMF (2 mL) was subjected to microwave irradiation at 110° C. for 1 hour. After cooling, the mixture was diluted with water and extracted with EtOAc. The combined organic layers were dried over anhydrous MgSO4 and concentrated in vacuo. The residue was purified by flash chromatography to afford the title compound as a white solid.

Workup

  1. customirradiation at 110° C. for 1 hour
  2. temperatureAfter cooling
  3. extractionextracted with EtOAc
  4. dry with materialThe combined organic layers were dried over anhydrous MgSO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-87a7dd84bd19447c9e3e78f5415f280d
Source dataset
uspto-grants-2015_02
Patent number
US08946439B2

Reaction notes

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