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Ethyl 2-bromothiazole-5-carboxylate → Ethyl 2-pyridin-2-yl-1,3-thiazole-5-carboxylate

HRID 1712929
Notes
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Reaction equation

HRID 1712929 reaction equation
Br[Zn][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][N:4]=1.Br[C:10]1[S:11][C:12]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:13][N:14]=1>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:4]1[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=1[C:10]1[S:11][C:12]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:13][N:14]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 2

HCID 3614103Ethyl 2-bromothiazole-5-carboxylateHCID 178419760HCID 178419760, compound

Product 1

HCID 53403816Ethyl 2-pyridin-2-yl-1,3-thiazole-5-carboxylate

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolvent2×
HCID 31275
1,4-Dioxane
Solvent

Procedure

A mixture of bromo(pyridine-2-yl)zinc (0.5 M in THF, 1.27 mL), ethyl 2-bromo-1,3-thiazole-5-carboxylate (0.063 mL, 0.42 mmol) and tetrakis(triphenylphosphine)palladium(0) (0.02 g, 0.02 mmol) in 1,4-dioxane (3 mL) and water (0.03 mL) was subjected to MWI at 120° C. for 10 min. The reaction mixture was diluted with water and extracted with EtOAc. The organic solutions were combined, dried over Na2SO4, filtered, and concentrated to give ethyl 2-pyridin-2-yl-1,3-thiazole-5-carboxylate (0.12 g) which was used without further purification. LCMS: (FA) ES+ 235.

Workup

  1. extractionextracted with EtOAc
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-18b9ee07fd114b68b8cf1707eaaa6374
Source dataset
uspto-grants-2010_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07795249B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes