Tetramethyltin → 4-Acetylamino-6-(4-chloro-2-fluoro-3-methoxyphenyl)-3-methylpyridine-2-carboxylic acid methyl ester

HRID 245290

반응식

HRID 245290 반응식
[CH3:1][O:2][C:3]([C:5]1[C:10](Cl)=[C:9]([NH:12][C:13](=[O:15])[CH3:14])[CH:8]=[C:7]([C:16]2[CH:21]=[CH:20][C:19]([Cl:22])=[C:18]([O:23][CH3:24])[C:17]=2[F:25])[N:6]=1)=[O:4].[CH3:26][Sn](C)(C)C>C(#N)C.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>[CH3:1][O:2][C:3]([C:5]1[C:10]([CH3:26])=[C:9]([NH:12][C:13](=[O:15])[CH3:14])[CH:8]=[C:7]([C:16]2[CH:21]=[CH:20][C:19]([Cl:22])=[C:18]([O:23][CH3:24])[C:17]=2[F:25])[N:6]=1)=[O:4]

참가 물질

5

반응물 2

HCID 11661TetramethyltinHCID 67210962Methyl 4-(acetylamino)-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)pyridine-2-carboxylate

생성물 1

HCID 594321274-Acetylamino-6-(4-chloro-2-fluoro-3-methoxyphenyl)-3-methylpyridine-2-carboxylic acid methyl ester수율 88.6%

시약·촉매·용매 2

HCID 178418476HCID 178418476, 화합물촉매HCID 6342Acetonitrile용매

반응 조건

온도
110 °C

실험 절차

4-Acetylamino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)-pyridine-2-carboxylic acid methyl ester (500 mg, 1.29 mmol), tetramethyltin (924 mg, 5.17 mmol), bis(triphenylphosphine)palladium(II) dichloride (91 mg, 0.129 mmol), and tetrabutylammonium triphenyldifluorosilicate (1.395 g, 2.58 mmol) were combined in 2 mL of acetonitrile and heated in a CEM microwave reactor at 110° C. for 15 min. The resulting reaction mixture was filtered and concentrated. This intermediate product was purified by flash chromatography on silica gel (ethyl acetate/hexane gradient) to yield the title compound (419 mg, 88% yield). mp 182-184° C.

후처리

  1. customThe resulting reaction mixture
  2. filtrationwas filtered
  3. concentrationconcentrated
  4. customThis intermediate product was purified by flash chromatography on silica gel (ethyl acetate/hexane gradient)

출처 및 근거

ORD 기록
ord-6dbffbc9a2b046a88853e735a257edb0
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08658791B2

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