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

HRID 1837454

Reaktionsgleichung

Reaktionsgleichung von HRID 1837454
[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]

Komponenten

6

Edukt 2

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

Produkt 1

HCID 22677349Methyl 4-acetamido-3-chloro-6-(2-thiazolyl)pyridine-2-carboxylateAusbeute 29,6 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418476HCID 178418476, VerbindungKatalysatorHCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-2830be1461e74111bc05fa55fd57f14f
Quelldatensatz
uspto-grants-2004_08
Patentnummer
US06784137B2

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