Sodium Carbonate → Sbb062309

HRID 2174182Notes

Reaction equation

HRID 2174182 reaction equation
Br[C:2]1[S:3][C:4]([C:8](=[O:10])[CH3:9])=[C:5]([CH3:7])[N:6]=1.[N:11]1[CH:16]=[CH:15][CH:14]=[C:13](B(O)O)[CH:12]=1.C(=O)([O-])[O-].[Na+].[Na+]>C(COC)OC.O.C(O)C>[N:11]1[CH:16]=[CH:15][CH:14]=[C:13]([C:2]2[S:3][C:4]([C:8](=[O:10])[CH3:9])=[C:5]([CH3:7])[N:6]=2)[CH:12]=1

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 27343783-Pyridinylboronic acidHCID 666448811-(2-Bromo-4-methylthiazol-5-YL)ethanone

Product 1

HCID 1485005Sbb062309

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

2-Bromo-4-methyl-5-acetylthiazole (12.0 g, 54.5 mmol) was dissolved in a mixture of dimethoxyethane (180 ml), water (76 ml) and ethanol (52 ml). To this solution was then added 3-pyridineboronic acid (20.1 g, 163.5 mmol), tetrakis(PPh3)palladium(0) (6.3 g, 5.4 mmol), and sodium carbonate (17.3 g, 163.5 mmol), and the reaction mixture was heated to 160° C. in a microwave oven for a period of 1 hour. The reaction was allowed to cool to ambient temperature, the solvents were removed by evaporation, the residue taken up in ethyl acetate, and the mixture filtered through silica gel and celite. The ethyl acetate was washed with water, dried over magnesium sulfate, and the solvent removed by evaporation. The crude product was purified by chromatograph and the product was obtained as a fawn colored solid. 1H NMR (CDCl3): 2.6 ppm (3H, s); 2.8 ppm (3H, s); 7.4 ppm (1H, m); 8.25 ppm (1H, m); 8.7 ppm (1H, m); 9.2 ppm (1H, m).

Workup

  1. customthe solvents were removed by evaporation
  2. filtrationthe mixture filtered through silica gel and celite
  3. washThe ethyl acetate was washed with water
  4. dry with materialdried over magnesium sulfate
  5. customthe solvent removed by evaporation
  6. customThe crude product was purified by chromatograph
  7. customthe product was obtained as a fawn

Sources & evidence

ORD record
ord-ce6a47c2dc834e6fa73f386600fbc821
Source dataset
uspto-grants-2015_06
Patent number
US09060519B2

Reaction notes

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