Triethylamine → benzyl 5-(1H-imidazol-5-yl)pent-4-ynoate

HRID 870582Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 870582
I[C:2]1[N:3]=[CH:4][NH:5][CH:6]=1.[C:7]([O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)(=[O:12])[CH2:8][CH2:9][C:10]#[CH:11].C(N(CC)CC)C>CN(C)C=O.O.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>[NH:3]1[C:2]([C:11]#[C:10][CH2:9][CH2:8][C:7]([O:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[O:12])=[CH:6][N:5]=[CH:4]1

Komponenten

8

Edukt 3

HCID 8471TriethylamineHCID 561097Benzyl pent-4-ynoateHCID 178506559HCID 178506559, Verbindung

Produkt 1

HCID 86726543benzyl 5-(1H-imidazol-5-yl)pent-4-ynoateAusbeute 69 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 178418476HCID 178418476, VerbindungKatalysatorHCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
75 °C

Versuchsvorschrift

Add bis(triphenylphosphine)palladium(II) chloride (0.14 g; 0.1 equiv; 0.20 mmoles) and copper(I) iodide (0.039 mg; 0.1 equiv; 0.20 mmoles) to a deoxygenated solution of 4-iodo-1H-imidazole (0.388 g; 1.0 equiv; 2.00 mmoles), benzyl pent-4-ynoate (0.376 g; 1.0 equiv; 2.00 mmoles), and triethylamine (0.84 mL; 3 equiv; 6.0 mmoles) in dimethylformamide (8 mL). Heat the mixture to 75° C. for 16 hours, then dilute the mixture with water (30 mL) and extract 3× with ethyl acetate. Wash the combined organic extracts with brine, dry over magnesium sulfate, filter, and concentrate to provide the crude product. Purify the crude product by column chromatography (0 to 10% methanol in dichloromethane) to afford benzyl 5-(1H-imidazol-5-yl)pent-4-ynoate (0.35 g; 69%) as a colorless oil: MS (m/z): 255(M+1).

Aufarbeitung

  1. extractionextract 3× with ethyl acetate
  2. washWash the combined organic extracts with brine
  3. dry with materialdry over magnesium sulfate
  4. filtrationfilter
  5. concentrationconcentrate
  6. customto provide the crude product
  7. customPurify the crude product by column chromatography (0 to 10% methanol in dichloromethane)

Quellen und Nachweise

ORD-Eintrag
ord-155eecd8ed134ae3b01bebfc5ff72213
Quelldatensatz
uspto-grants-2015_03
Patentnummer
US08969555B2

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