Methyl 2-bromothiazole-5-carboxylate → Methyl 2-(pyridin-2-yl)thiazole-5-carboxylate

HRID 1260321Notes

Reaction equation

HRID 1260321 reaction equation
[CH3:1][O:2][C:3]([C:5]1[S:9][C:8](Br)=[N:7][CH:6]=1)=[O:4].Br[Zn][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=1>C1COCC1.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>[CH3:1][O:2][C:3]([C:5]1[S:9][C:8]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=2)=[N:7][CH:6]=1)=[O:4]

Participants

5

Reactant 2

HCID 2773502Methyl 2-bromothiazole-5-carboxylateHCID 178419760HCID 178419760, compound

Product 1

HCID 57688443Methyl 2-(pyridin-2-yl)thiazole-5-carboxylate

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of 2-bromo-1,3-thiazole-5-carboxylic acid methyl ester (0.5 g, 2.25 mmol) and Pd(PPh3)4 (0.13 g, 0.11 mmol) in THF (12.5 ml) was added bromo-(pyridine-2-yl)-zinc (6.75 ml, 0.5M THF solution) under inert gas atmosphere. The reaction mixture was irradiated under microwave conditions at 120° C. for 10 min. The solvent was removed and the product was obtained after purification by silica gel chromatography using a heptane/ethyl acetate gradient as yellow crystals (0.34 g, 68%) MS: M=221.2 (M+H)+

Workup

  1. customThe reaction mixture was irradiated under microwave conditions at 120° C. for 10 min
  2. customThe solvent was removed
  3. customthe product was obtained
  4. customafter purification by silica gel chromatography

Sources & evidence

ORD record
ord-3fbe966f1e4e4e9fb0b81847b28be99d
Source dataset
uspto-grants-2013_06
Patent number
US08470820B2

Reaction notes

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