Potassium Carbonate → Methyl 2-(3-methylphenyl)-5-methyl-1,3-thiazole-4-carboxylate

HRID 1816628Notes

Reaction equation

HRID 1816628 reaction equation
Br[C:2]1[S:3][C:4]([CH3:11])=[C:5]([C:7]([O:9][CH3:10])=[O:8])[N:6]=1.Cl[C:13]1[CH:14]=[C:15](OB(O)O)[CH:16]=[CH:17][CH:18]=1.[C:23](=O)([O-])[O-].[K+].[K+]>C1(C)C=CC=CC=1>[CH3:23][C:13]1[CH:14]=[C:15]([C:2]2[S:3][C:4]([CH3:11])=[C:5]([C:7]([O:9][CH3:10])=[O:8])[N:6]=2)[CH:16]=[CH:17][CH:18]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 22493969Methyl 2-bromo-5-methyl-1,3-thiazole-4-carboxylateHCID 22494354m-Chlorophenylboric acid

Product 1

HCID 22494233Methyl 2-(3-methylphenyl)-5-methyl-1,3-thiazole-4-carboxylateYield 69.7%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

0.3 g of methyl 2-bromo-5-methyl-1,3-thiazole-4-carboxylate and 0.2 g of 3-chlorophenylboric acid were dissolved in toluene, and 0.15 g of tetrakistriphenyl phosphine and 0.7 g of potassium carbonate were added. The reaction solution was heated under reflux for 4 hours in a nitrogen atmosphere. The reaction solution was cooled, filtered through Celite and evapoarated. The residue was purified by silica gel column chromatography, to give 0.2 g of methyl 2-(3-methylphenyl)-5-methyl-1,3-thiazole-4-carboxylate.

Workup

  1. temperatureThe reaction solution was heated
  2. temperatureunder reflux for 4 hours in a nitrogen atmosphere
  3. temperatureThe reaction solution was cooled
  4. filtrationfiltered through Celite
  5. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-82c92f10bda14107947b8ac3f149493f
Source dataset
uspto-grants-2005_04
Patent number
US06884821B1

Reaction notes

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