Triphenylphosphine → HCID 178472394, Verbindung

HRID 1616340

Reaktionsgleichung

Reaktionsgleichung von HRID 1616340
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][N:6]=[CH:5]2.O[C@H:12]1[CH2:17][CH2:16][C@H:15]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH2:14][CH2:13]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O>C1COCC1>[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([C@@H:12]1[CH2:17][CH2:16][C@H:15]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH2:14][CH2:13]1)[N:6]=[CH:5]2

Komponenten

6

Edukt 4

HCID 11776TriphenylphosphineHCID 7619295-bromo-1H-indazoleHCID 5462977Diethyl azodicarboxylateHCID 178472487HCID 178472487, Verbindung

Produkt 1

HCID 178472394HCID 178472394, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

A solution of 5-bromoindazole (5.00 g), ethyl trans-4-hydroxycyclohexanecarboxylate (8.73 g), triphenylphosphine (13.3 g) in THF (150 mL) was stirred at 0° C. for 15 minutes. To the reaction solution was added dropwise diethylazodicarboxylate (9.03 g) under nitrogen atmosphere at 0° C., and the mixture was stirred at 50° C. for 13 hours. Then, the solvent was removed out, and ethyl acetate (100 mL) and petroleum ether (30 mL) were added thereto. The mixture was stirred at room temperature for 2 hours. The reaction solution was filtered, the solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate:petroleum ether=1:80-1:15 as the eluting solvent) to give Compound Q14 (3.50 g).

Aufarbeitung

  1. customThen, the solvent was removed out
  2. additionethyl acetate (100 mL) and petroleum ether (30 mL) were added
  3. stirringThe mixture was stirred at room temperature for 2 hours
  4. filtrationThe reaction solution was filtered
  5. customthe solvent was evaporated under reduced pressure
  6. customthe residue was purified by silica gel column chromatography (ethyl acetate
  7. custompetroleum ether=1:80-1:15 as the eluting solvent) to give Compound Q14 (3.50 g)

Quellen und Nachweise

ORD-Eintrag
ord-8cc1ba0e76be440f8c2b13308be17604
Quelldatensatz
uspto-grants-2014_07
Patentnummer
US08765786B2

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