2-(Tributylstannyl)pyridine → HCID 58765662, compound

HRID 860694Notes

Reaction equation

HRID 860694 reaction equation
[CH3:1][O:2][C:3](=[O:30])[CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][CH2:13][CH:14]([C:16]2[N:17]=[C:18]([C:22]3[CH:27]=[CH:26][C:25](Br)=[CH:24][CH:23]=3)[O:19][C:20]=2[CH3:21])[CH3:15])=[CH:8][C:7]=1[CH3:29].C([Sn](CCCC)(CCCC)[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][N:37]=1)CCC>C1(C)C=CC=CC=1>[CH3:1][O:2][C:3](=[O:30])[CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][CH2:13][CH:14]([C:16]2[N:17]=[C:18]([C:22]3[CH:27]=[CH:26][C:25]([C:36]4[CH:41]=[CH:40][CH:39]=[CH:38][N:37]=4)=[CH:24][CH:23]=3)[O:19][C:20]=2[CH3:21])[CH3:15])=[CH:8][C:7]=1[CH3:29]

Participants

4

Reactant 2

HCID 6077842-(Tributylstannyl)pyridineHCID 58765687HCID 58765687, compound

Product 1

HCID 58765662HCID 58765662, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

3-(4-{2-[2-(4-Bromo-phenyl)-5-methyl-oxazol-4-yl]-propoxy}-2-methylphenyl)-propionic acid methyl ester (592 mg, 1.25 mmol) is dissolved in anhydrous toluene (5 mL), degassed, and filled with nitrogen three times. Palladium tetrakis triphenyl phosphine [Pd(PPh3)4, 25 mg, 0.025 mmol] is added, and the degassing procedure is repeated. 2-tributylstannylpyridine (635 uL, 2.5 mmol) is then added via syringe and the reaction is heated to reflux. The reaction is monitored by HPLC. Upon complete consumption of starting material, the reaction is allowed to cool to room temperature and diluted with ethyl acetate. Celite is added and the mixture is filtered and rinsed with more ethyl acetate and water. The solution is further diluted with water and the two phases are separated. The organic layer is washed with water and brine, dried over anhydrous sodium sulfate, filtered, and concentrated. The pure 3-(2-Methyl-4-{2-[5-methyl-2-(4-pyridin-2-yl-phenyl)-oxazol-4-yl]-propoxy}-phenyl)-propionic acid methyl ester is obtained after column chromatography.

Workup

  1. customdegassed
  2. additionfilled with nitrogen three times
  3. temperaturethe reaction is heated to reflux
  4. customUpon complete consumption of starting material
  5. additiondiluted with ethyl acetate
  6. additionCelite is added
  7. filtrationthe mixture is filtered
  8. washrinsed with more ethyl acetate and water
  9. additionThe solution is further diluted with water
  10. customthe two phases are separated
  11. washThe organic layer is washed with water and brine
  12. dry with materialdried over anhydrous sodium sulfate
  13. filtrationfiltered
  14. concentrationconcentrated

Sources & evidence

ORD record
ord-2a92afa126164aa994fadc10f82b1d08
Source dataset
uspto-grants-2006_12
Patent number
US07153878B2

Reaction notes

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