Diisopropylamine → 2-Amino-4-phenylethynyl-thiophene-3-carboxylic acid ethyl ester

HRID 1244162ノート

反応式

HRID 1244162 の反応式
[CH2:1]([O:3][C:4]([C:6]1[C:10]([C:11]#[CH:12])=[CH:9][S:8][C:7]=1[NH2:13])=[O:5])[CH3:2].I[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C(NC(C)C)(C)C>CC#N.[Cu](I)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>[CH2:1]([O:3][C:4]([C:6]1[C:10]([C:11]#[C:12][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[CH:9][S:8][C:7]=1[NH2:13])=[O:5])[CH3:2]

参加物

7

反応物 3

HCID 7912DiisopropylamineHCID 11575IodobenzeneHCID 860308212-Amino-4-ethynyl-thiophene-3-carboxylic acid ethyl ester

生成物 1

HCID 696073742-Amino-4-phenylethynyl-thiophene-3-carboxylic acid ethyl ester収率 78%

試薬・触媒・溶媒 3

HCID 83717Copper iodide触媒HCID 178418476HCID 178418476、化合物触媒HCID 6342Acetonitrile溶媒

実験手順

2-Amino-4-ethynyl-thiophene-3-carboxylic acid ethyl ester (0.075 g, 0.385 mmol) was dissolved in anhydrous CH3CN (2.0 mL). This was treated with iodobenzene (0.129 mL, 1.15 mmol) followed by diisopropylamine (0.272 mL, 1.92 mmol). The solution was then degassed and treated with copper iodide (0.0018 g, 0.010 mmol) and dichlorobis(triphenylphosphine)palladium(II) (0.014 g, 0.019 mmol). The reaction was then stirred at room temperature for 30 min. The reaction was concentrated in vacuo. The crude product was purified by flash chromatography (SiO2, 15 EtOAc/85 hexanes) to afford the title compound (0.081 g, 78%). MS m/e (CI) 272.0 (M+H)+.

後処理

  1. customThe solution was then degassed
  2. concentrationThe reaction was concentrated in vacuo
  3. customThe crude product was purified by flash chromatography (SiO2, 15 EtOAc/85 hexanes)

出典と根拠

ORDレコード
ord-1353930791ae4fc8af2e7ac1132d4775
出典データセット
uspto-grants-2006_10
特許番号
US07119205B2

反応ノート

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