Trimethyl((tributylstannyl)ethynyl)silane → HCID 59432138、化合物

HRID 245294

反応式

HRID 245294 の反応式
[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][Si:27]([CH3:44])([CH3:43])[C:28]#[C:29][Sn](CCCC)(CCCC)CCCC>ClCCCl.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]([C:29]#[C:28][Si:27]([CH3:44])([CH3:43])[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]

参加物

5

反応物 2

HCID 639663Trimethyl((tributylstannyl)ethynyl)silaneHCID 67210962Methyl 4-(acetylamino)-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)pyridine-2-carboxylate

生成物 1

HCID 59432138HCID 59432138、化合物収率 21.2%

試薬・触媒・溶媒 2

HCID 178418476HCID 178418476、化合物触媒HCID 111,2-Dichloroethane溶媒

反応条件

温度
130 °C

実験手順

4-Acetylamino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)-pyridine-2-carboxylic acid methyl ester (0.8 g, 2.061 mmol), trimethyl((tributylstannyl)ethynyl)silane (1.596 g, 4.12 mmol), and bis(triphenylphosphine)palladium(II) dichloride (0.145 g, 0.206 mmol) were combined in 1,2-dichloroethane (2 mL) and heated in a CEM microwave reactor at 130° C. for 15 min. The cooled reaction mixture was purified by flash chromatography on silica gel (hexane/ethyl acetate gradient) to yield the title compound (0.196 g, 21.1% yield). 1H NMR (CDCl3) δ 9.03 (s, 1H), 8.4 (br s, 1H), 7.67 (m, 1H), 7.24 (m, 1H), 4.0 (s, 3H), 3.99 (d, 3H), 2.29 (s, 3H), 0.36 (s, 9H).

後処理

  1. customThe cooled reaction mixture
  2. customwas purified by flash chromatography on silica gel (hexane/ethyl acetate gradient)

出典と根拠

ORDレコード
ord-10ad08901c644a4b96f848dec48b2c31
出典データセット
uspto-grants-2014_02
特許番号
US08658791B2

関連ノート

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