Toluene → HCID 69139173, compound

HRID 854586Notes

Reaction equation

HRID 854586 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:9][C:10]([CH3:28])=[C:11]([CH2:13][CH2:14][O:15][C:16]3[CH:21]=[CH:20][C:19]([CH2:22][CH2:23][C:24]([OH:26])=[O:25])=[C:18]([CH3:27])[CH:17]=3)[N:12]=2)=[CH:4][CH:3]=1.C([Sn](CCCC)(CCCC)[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][N:35]=1)CCC.[C:48]1(C)C=CC=CC=1>>[CH3:48][O:26][C:24](=[O:25])[CH2:23][CH2:22][C:19]1[CH:20]=[CH:21][C:16]([O:15][CH2:14][CH2:13][C:11]2[N:12]=[C:8]([C:5]3[CH:6]=[CH:7][C:2]([C:34]4[CH:39]=[CH:38][CH:37]=[CH:36][N:35]=4)=[CH:3][CH:4]=3)[S:9][C:10]=2[CH3:28])=[CH:17][C:18]=1[CH3:27]

Participants

4

Reactant 3

HCID 1140TolueneHCID 6077842-(Tributylstannyl)pyridineHCID 69141092HCID 69141092, compound

Product 1

HCID 69139173HCID 69139173, compound

Procedure

3-(4-{2-[2-(4-Bromo-phenyl)-5-methyl-thiazol-4-yl]-ethoxy}-2-methyl-phenyl)-propionic acid (100 mg, 0.21 mmol) is dissolved in anhydrous toluene (1 mL), degassed, and filled with nitrogen three times. Palladium tetrakis triphenyl phosphine [Pd(PPh3)4, 21 mg, 0.0021 mmol] is added, and the degassing procedure is repeated. 2-tributylstannylpyridine (63 uL, 0.25 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)-thiazol-4-yl]-ethoxy}-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-dccfd18c658645d28922788c6c7d00e6
Source dataset
uspto-grants-2007_08
Patent number
US07259175B2

Reaction notes

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