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

HRID 1244162노트

반응식

HRID 1244162 반응식
[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]

참가 물질

7

반응물 3

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

생성물 1

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

시약·촉매·용매 3

HCID 83717Copper iodide촉매HCID 178418476HCID 178418476, 화합물촉매HCID 6342Acetonitrile용매

실험 절차

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)+.

후처리

  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)

출처 및 근거

ORD 기록
ord-1353930791ae4fc8af2e7ac1132d4775
출처 데이터셋
uspto-grants-2006_10
특허 번호
US07119205B2

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