Sodium Carbonate → HCID 69141239, compound

HRID 854589Notes

Reaction equation

HRID 854589 reaction equation
[CH3:1][O:2][C:3](=[O:29])[CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][CH2:13][CH2:14][C:15]2[N:16]=[C:17]([C:21]3[CH:26]=[CH:25][C:24](Br)=[CH:23][CH:22]=3)[S:18][C:19]=2[CH3:20])=[CH:8][C:7]=1[CH3:28].[N:30]1[CH:35]=[CH:34][CH:33]=[C:32](B(O)O)[CH:31]=1.C(=O)([O-])[O-].[Na+].[Na+].B(O)O>C1(C)C=CC=CC=1.C(O)C>[CH3:1][O:2][C:3](=[O:29])[CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][CH2:13][CH2:14][C:15]2[N:16]=[C:17]([C:21]3[CH:26]=[CH:25][C:24]([C:32]4[CH:31]=[N:30][CH:35]=[CH:34][CH:33]=4)=[CH:23][CH:22]=3)[S:18][C:19]=2[CH3:20])=[CH:8][C:7]=1[CH3:28]

Participants

7

Reactant 4

HCID 10340Sodium CarbonateHCID 61668Boronic AcidHCID 27343783-Pyridinylboronic acidHCID 69141122HCID 69141122, compound

Product 1

HCID 69141239HCID 69141239, compoundYield 50%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

3-(4-{2-[2-(4-Bromo-phenyl)-5-methyl-thiazol-4-yl]-ethoxy}-2-methyl-phenyl)-propionic acid methyl ester (100 mg, 0.200 mmol) is dissolved in toluene (1 mL), degassed, and filled with nitrogen three times. Palladium tetrakistriphenyl phosphine (10 mg, 0.010 mmol), 3-pyridylboronic acid (31 mg, 0.250 mmol), and sodium carbonate (100 uL of a 10M solution, 0.400 mmol) are added, and the degassing procedure is repeated. Ethanol (1 mL) is added to dissolve the boronic acid. The reaction is heated to 100° C. and 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-3-yl-phenyl)-thiazol-4-yl]-ethoxy}-phenyl)-propionic acid methyl ester (47 mg, 0.100 mmol) is obtained after column chromatography (50% yield).

Workup

  1. customdegassed
  2. additionfilled with nitrogen three times
  3. customUpon complete consumption of starting material
  4. temperatureto cool to room temperature
  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-68e6167b7e8b4a3eae0217107d234f56
Source dataset
uspto-grants-2007_08
Patent number
US07259175B2

Reaction notes

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