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

HRID 1837454

反応式

HRID 1837454 の反応式
[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]

参加物

6

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 178418476HCID 178418476、化合物触媒HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-2830be1461e74111bc05fa55fd57f14f
出典データセット
uspto-grants-2004_08
特許番号
US06784137B2

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