Propargyl bromide → HCID 86759654, Verbindung

HRID 2121889

Reaktionsgleichung

Reaktionsgleichung von HRID 2121889
[OH:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[N:7][N:8]2[CH2:11][C@@H:12]([NH:14][C:15](=[O:24])[O:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH3:13])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:31](Br)[C:32]#[CH:33]>CC(C)=O>[CH3:13][C@H:12]([NH:14][C:15](=[O:24])[O:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[CH2:11][N:8]1[C:9]2[C:5](=[CH:4][CH:3]=[C:2]([O:1][CH2:33][C:32]#[CH:31])[CH:10]=2)[CH:6]=[N:7]1

Komponenten

5

Edukt 3

HCID 7842Propargyl bromideHCID 11430Potassium CarbonateHCID 135487328Benzyl (S)-2-(6-hydroxy-1H-indazol-1-yl)-1-methylethylcarbamate

Produkt 1

HCID 86759654HCID 86759654, VerbindungAusbeute 74 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Versuchsvorschrift

A solution of the product from Step A (2.88 g, 8.86 mmol) in acetone (100 mL) was degassed with reduced pressure and nitrogen. Powdered potassium carbonate (1.35 g, 9.75 mmol) and propargyl bromide (80% by weight in toluene, 0.99 mL, 8.86 mmol) were added the mixture was refluxed for 24 hours. The cooled reaction mixture was filtered and the filtrate was evaporated to a yellow oil (3.15 g) which was purified by chromatography (silica, 20% to 50% ethyl acetate in hexane) to give a white solid (2.37 g, 74%): mp 104-106° C.; LC/MS (+APCI) m/z 364 (M+H).

Aufarbeitung

  1. temperaturewas refluxed for 24 hours
  2. customThe cooled reaction mixture
  3. filtrationwas filtered
  4. customthe filtrate was evaporated to a yellow oil (3.15 g) which
  5. customwas purified by chromatography (silica, 20% to 50% ethyl acetate in hexane)

Quellen und Nachweise

ORD-Eintrag
ord-39f63cc8063c4462a9d975a0aeeaee6e
Quelldatensatz
uspto-grants-2004_02
Patentnummer
US06696476B2

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