3-Ethyl-1-pentyn-3-ol → 7-{[4-(1-ethyl-1-hydroxypropyl)-1H-1,2,3-triazol-1-yl]methyl}-4-phenylquinoline-2-carbonitrile

HRID 2422531Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2422531
[N:1]([CH2:4][C:5]1[CH:14]=[C:13]2[C:8]([C:9]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[CH:10][C:11]([C:15]#[N:16])=[N:12]2)=[CH:7][CH:6]=1)=[N+:2]=[N-:3].[CH2:23]([C:25]([OH:30])([CH2:28][CH3:29])[C:26]#[CH:27])[CH3:24].C(N(C(C)C)CC)(C)C>C1COCC1.[Cu](I)I>[CH2:26]([C:25]([C:23]1[N:3]=[N:2][N:1]([CH2:4][C:5]2[CH:14]=[C:13]3[C:8]([C:9]([C:17]4[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=4)=[CH:10][C:11]([C:15]#[N:16])=[N:12]3)=[CH:7][CH:6]=2)[CH:24]=1)([OH:30])[CH2:28][CH3:29])[CH3:27]

Komponenten

6

Edukt 3

HCID 226983-Ethyl-1-pentyn-3-olHCID 81531DiisopropylethylamineHCID 59774860HCID 59774860, Verbindung

Produkt 1

HCID 250576617-{[4-(1-ethyl-1-hydroxypropyl)-1H-1,2,3-triazol-1-yl]methyl}-4-phenylquinoline-2-carbonitrile

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 83717Copper iodideKatalysatorHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A mixture of 7-(azidomethyl)-4-phenylquinoline-2-carbonitrile (100 mg, 0.35 mmol), 3-ethylpent-1-yn-3-ol (47 mg, 0.42 mmol), copper iodide (100 mg, 0.52 mmol) and diisopropylethylamine (305 μL, 1.75 mmol) in THF (4 mL) was stirred at rt for 6 h. The reaction was quenched with saturated aqueous NH4Cl and extracted with EtOAc. The combined organic layers were washed with brine, dried over Na2SO4, filtered and concentrated under reduced pressure. Purification on silica gel (eluting with acetone/dichloromethane, 2:8) gave the title compound. MS (+ESI): 398 (M+H)+.

Aufarbeitung

  1. customThe reaction was quenched with saturated aqueous NH4Cl
  2. extractionextracted with EtOAc
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customPurification on silica gel (eluting with acetone/dichloromethane, 2:8)

Quellen und Nachweise

ORD-Eintrag
ord-e99e92ebb877478381c7730ad7e782a5
Quelldatensatz
uspto-grants-2011_06
Patentnummer
US07960409B2

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