Triethylamine → 5-Chloro-3-((trimethylsilyl)ethynyl)pyridin-2-amine

HRID 402595

反応式

HRID 402595 の反応式
[NH2:1][C:2]1[C:7](I)=[CH:6][C:5]([Cl:9])=[CH:4][N:3]=1.C(N(CC)CC)C.[C:17]([Si:19]([CH3:22])([CH3:21])[CH3:20])#[CH:18]>O1CCCC1.C(OCC)C.[Cu]I.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>[NH2:1][C:2]1[C:7]([C:18]#[C:17][Si:19]([CH3:22])([CH3:21])[CH3:20])=[CH:6][C:5]([Cl:9])=[CH:4][N:3]=1

参加物

8

反応物 3

HCID 8471TriethylamineHCID 66111TrimethylsilylacetyleneHCID 110760102-Amino-5-chloro-3-iodopyridine

生成物 1

HCID 247294655-Chloro-3-((trimethylsilyl)ethynyl)pyridin-2-amine収率 109.9%

試薬・触媒・溶媒 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 178418476HCID 178418476、化合物触媒HCID 3283Diethyl Ether溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

Under a nitrogen atmosphere, to a solution of 2-amino-5-chloro-3-iodopyridine (4.2 g, 0.017 mol), copper(I) iodide (0.032 g, 0.17 mmol) and triethylamine (7.0 mL, 0.050 mol) in anhydrous tetrahydrofuran (10 mL), dichlorobis(triphenylphosphine)palladium(II) (0.12 g, 0.17 mmol) and ethynyl trimethylsilane (3.0 mL, 0.021 mol) were added and the mixture was stirred at ambient temperature for 2 h. The reaction mixture was diluted with diethyl ether and removed the precipitate by filtration with C elite. The filtrate was concentrated to afford 2-amino-5-chloro-3-[(trimethylsilyl)ethynyl]pyridine as solid (4.2 g).

後処理

  1. customremoved the precipitate
  2. filtrationby filtration with C elite
  3. concentrationThe filtrate was concentrated

出典と根拠

ORDレコード
ord-84fa41631148433bab00c109d60ee98d
出典データセット
uspto-grants-2014_06
特許番号
US08742113B2

関連ノート

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