2-(Trimethylstannyl)-1,3-thiazole → Methyl 4-acetamido-3-chloro-6-(2-thiazolyl)pyridine-2-carboxylate

HRID 1837454Notes

Reaction equation

HRID 1837454 reaction equation
[C:1]([NH:4][C:5]1[CH:10]=[C:9](Cl)[N:8]=[C:7]([C:12]([O:14][CH3:15])=[O:13])[C:6]=1[Cl:16])(=[O:3])[CH3:2].C[Sn](C)(C)[C:19]1[S:20][CH:21]=[CH:22][N:23]=1>O1CCCC1.O.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>[C:1]([NH:4][C:5]1[CH:10]=[C:9]([C:19]2[S:20][CH:21]=[CH:22][N:23]=2)[N:8]=[C:7]([C:12]([O:14][CH3:15])=[O:13])[C:6]=1[Cl:16])(=[O:3])[CH3:2]

Participants

6

Reactant 2

HCID 129566412-(Trimethylstannyl)-1,3-thiazoleHCID 22677481Methyl 4-acetamido-3,6-dichloropyridine-2-carboxylate

Product 1

HCID 22677349Methyl 4-acetamido-3-chloro-6-(2-thiazolyl)pyridine-2-carboxylateYield 29.6%

Reagents, catalysts & solvents 3

HCID 178418476HCID 178418476, compoundCatalystHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of methyl 4-acetamido-3,6-dichloropyridine-2-carboxylate (1.0 g, 4.05 mmol), 2-(trimethylstannyl)thiazole (2.9 g, 17.3 mmol) and dichlorobis(triphenylphosphine)palladium(II) (0.4 g, 0.6 mmol) in tetrahydrofuran (75 mL) was heated under reflux for four hours. The reaction was diluted with water (100 mL) and extracted with ethyl acetate (2×100 mL). The organic phase was dried (MgSO4) and concentrated. The crude product was purified by column chromatography (50% ethyl acetate in hexane) to give methyl 4-acetamido-3-chloro-6-(2-thiazolyl)pyridine-2-carboxylate (0.38 g, 1.2 mmol), mp 187-8° C.

Workup

  1. temperatureunder reflux for four hours
  2. extractionextracted with ethyl acetate (2×100 mL)
  3. dry with materialThe organic phase was dried (MgSO4)
  4. concentrationconcentrated
  5. customThe crude product was purified by column chromatography (50% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-2830be1461e74111bc05fa55fd57f14f
Source dataset
uspto-grants-2004_08
Patent number
US06784137B2

Reaction notes

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