Water → Ethyl 2,5'-bi-1,3-thiazole-4'-carboxylate

HRID 383933Notes

Reaction equation

HRID 383933 reaction equation
Br[C:2]1[S:6][CH:5]=[N:4][C:3]=1[C:7]([O:9][CH2:10][CH3:11])=[O:8].C([Sn](CCCC)(CCCC)[C:17]1[S:18][CH:19]=[CH:20][N:21]=1)CCC.O>C1(C)C=CC=CC=1.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[S:18]1[CH:19]=[CH:20][N:21]=[C:17]1[C:2]1[S:6][CH:5]=[N:4][C:3]=1[C:7]([O:9][CH2:10][CH3:11])=[O:8]

Participants

6

Reactant 3

HCID 962WaterHCID 27632592-(Tributylstannyl)-1,3-thiazoleHCID 12361218Ethyl 5-bromo-1,3-thiazole-4-carboxylate

Product 1

HCID 59291355Ethyl 2,5'-bi-1,3-thiazole-4'-carboxylate

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 1140TolueneSolvent

Procedure

To a solution of ethyl 5-bromo-1,3-thiazole-4-carboxylate in toluene were added 2-(tributylstannyl)-1,3-thiazole and PdCl2(PPh3)2, followed by heating under reflux for 6 hours. Water was added thereto and the aqueous layer was extracted with EtOAc. The organic layer was dried over MgSO4, filtered, and concentrated under reduced pressure. The residue was purified by medium-pressure preparative liquid chromatography (silica gel, YAMAZEN YFLC WPrep2XY, hexane: EtOAc) to obtain ethyl 2,5′-bi-1,3-thiazole-4′-carboxylate as a yellow solid.

Workup

  1. temperatureby heating
  2. temperatureunder reflux for 6 hours
  3. extractionthe aqueous layer was extracted with EtOAc
  4. dry with materialThe organic layer was dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by medium-pressure preparative liquid chromatography (silica gel, YAMAZEN YFLC WPrep2XY, hexane: EtOAc)

Sources & evidence

ORD record
ord-2d3cc926eced40e69b1b6f5f1e2d7c95
Source dataset
uspto-grants-2013_02
Patent number
US08367696B2

Reaction notes

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