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

HRID 1244162Notes

Reaction equation

HRID 1244162 reaction equation
[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]

Participants

7

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 3

HCID 83717Copper iodideCatalystHCID 178418476HCID 178418476, compoundCatalystHCID 6342AcetonitrileSolvent

Procedure

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)+.

Workup

  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)

Sources & evidence

ORD record
ord-1353930791ae4fc8af2e7ac1132d4775
Source dataset
uspto-grants-2006_10
Patent number
US07119205B2

Reaction notes

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