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

HRID 1837454

반응식

HRID 1837454 반응식
[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]

참가 물질

6

반응물 2

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

생성물 1

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

시약·촉매·용매 3

HCID 178418476HCID 178418476, 화합물촉매HCID 962Water용매HCID 8028Tetrahydrofuran용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-2830be1461e74111bc05fa55fd57f14f
출처 데이터셋
uspto-grants-2004_08
특허 번호
US06784137B2

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