Potassium Carbonate → 2-Pyridin-4-yl-thiazole-5-carboxylic acid

HRID 1712928Notes

Reaction equation

HRID 1712928 reaction equation
Br[C:2]1[S:3][C:4]([C:7]([O:9]CC)=[O:8])=[CH:5][N:6]=1.[N:12]1[CH:17]=[CH:16][C:15](B(O)O)=[CH:14][CH:13]=1.C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[N:12]1[CH:17]=[CH:16][C:15]([C:2]2[S:3][C:4]([C:7]([OH:9])=[O:8])=[CH:5][N:6]=2)=[CH:14][CH:13]=1

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 2734379(Pyridin-4-yl)boronic acidHCID 3614103Ethyl 2-bromothiazole-5-carboxylate

Product 1

HCID 219285322-Pyridin-4-yl-thiazole-5-carboxylic acid

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolvent2×HCID 312751,4-DioxaneSolvent

Procedure

A mixture of ethyl 2-bromo-1,3-thiazole-5-carboxylate (0.095 mL, 0.64 mmol), pyridine-4-ylboronic acid (0.094 g, 0.76 mmol), tetrakis(triphenylphosphine)palladium(0) (0.007 g, 0.006 mmol), and potassium carbonate (0.263 g, 1.91 mmol) in 1,4-dioxane (10 mL) and water (0.5 mL) was subjected to MWI at 160° C. for 20 min. The reaction mixture was diluted with water and extracted with EtOAc. The organic solutions were combined, acidified and concentrated. The residue was dissolved in EtOAc and brine was added. The organic solution was separated, dried over Na2SO4, filtered and concentrated to give 2-pyridin-4-yl-1,3-thiazole-5-carboxylic acid which was used without further purification. LCMS: (FA) ES+ 207.

Workup

  1. extractionextracted with EtOAc
  2. concentrationconcentrated
  3. dissolutionThe residue was dissolved in EtOAc
  4. additionbrine was added
  5. customThe organic solution was separated
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-dc986272530249b4a4125c0511b495aa
Source dataset
uspto-grants-2010_09
Patent number
US07795249B2

Reaction notes

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