Diisopropylethylamine → N-(1-(4-Ethynylphenyl)propan-2-yl)cyclopropanecarboxamide

HRID 76167Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 76167
I[C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH:9]([NH:11][C:12]([CH:14]2[CH2:16][CH2:15]2)=[O:13])[CH3:10])=[CH:4][CH:3]=1.[Si](C#C)([C:20](C)(C)[CH3:21])(C)C.CCN(C(C)C)C(C)C.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1.O.C(Cl)Cl.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.[Cu]I>[C:20]([C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH:9]([NH:11][C:12]([CH:14]2[CH2:16][CH2:15]2)=[O:13])[CH3:10])=[CH:4][CH:3]=1)#[CH:21]

Komponenten

10

Edukt 4

HCID 81531DiisopropylethylamineHCID 2724141Tetrabutylammonium FluorideHCID 2757281(tert-Butyldimethylsilyl)acetyleneHCID 66610754N-(1-(4-Iodophenyl)propan-2-YL)cyclopropanecarboxamide

Produkt 1

HCID 86669619N-(1-(4-Ethynylphenyl)propan-2-yl)cyclopropanecarboxamide

Reagenzien, Katalysatoren, Lösungsmittel 5

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 178418476HCID 178418476, VerbindungKatalysatorHCID 962WaterLösungsmittel2×HCID 6344DichloromethaneLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To 900 mg (2.73 mmol) N-(1-(4-iodophenyl)propan-2-yl)cyclopropanecarboxamide (I52.3) and 0.56 mL (3.01 mmol) (tert-butyldimethylsilyl)acetylene in 5 mL THF at 0° C. are added 0.77 mL (5.48 mmol) DIPEA, 96.1 mg (0.14 mmol) bis(triphenyl-phosphine)dichloropalladium and 53.1 mg (0.28 mmol) CuI, and the reaction mixture is stirred at r.t. over night. The mixture is diluted with water and extracted with DCM (2×). The organic layer is dried with Na2SO4 and the solvent is removed in vacuo. The residue is purified by column chromatography (silica gel, DCM/MeOH 98/2) to yield the silylated compound. To this substance in DCM are added 949 mg (3.01 mmol) TBAF*3H2O and the mixture is stirred at r.t. for 3 h. The mixture is diluted with water and extracted with DCM. The organic layer is dried with Na2SO4 and the solvent is removed in vacuo. The crude product is purified by column chromatography (silica gel, DCM/MeOH 98/2).

Aufarbeitung

  1. extractionextracted with DCM (2×)
  2. dry with materialThe organic layer is dried with Na2SO4
  3. customthe solvent is removed in vacuo
  4. customThe residue is purified by column chromatography (silica gel, DCM/MeOH 98/2)
  5. customto yield the silylated compound
  6. stirringthe mixture is stirred at r.t. for 3 h
  7. extractionextracted with DCM
  8. dry with materialThe organic layer is dried with Na2SO4
  9. customthe solvent is removed in vacuo
  10. customThe crude product is purified by column chromatography (silica gel, DCM/MeOH 98/2)

Quellen und Nachweise

ORD-Eintrag
ord-a3d7f4c8de484fc5aaa3b341922fd5d0
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08835472B2

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