Benzyl azide → 1-Benzyl-5-(4-fluorophenyl)-4-(tributylstannyl)-1H-1,2,3-triazole

HRID 240770Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 240770
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]#[CH:9])=[CH:4][CH:3]=1.[CH2:10]([Sn:14]([CH2:22][CH2:23][CH2:24][CH3:25])([CH2:18][CH2:19][CH2:20][CH3:21])N(C)C)[CH2:11][CH2:12][CH3:13].[CH2:26]([N:33]=[N+:34]=[N-:35])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>>[CH2:26]([N:33]1[C:8]([C:5]2[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=2)=[C:9]([Sn:14]([CH2:10][CH2:11][CH2:12][CH3:13])([CH2:18][CH2:19][CH2:20][CH3:21])[CH2:22][CH2:23][CH2:24][CH3:25])[N:35]=[N:34]1)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Komponenten

4

Edukt 3

HCID 12152Benzyl azideHCID 5226271-Ethynyl-4-fluorobenzeneHCID 11034994Dimethylaminotri-n-butyltin

Produkt 1

HCID 689915921-Benzyl-5-(4-fluorophenyl)-4-(tributylstannyl)-1H-1,2,3-triazole

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

4-Fluorophenyl acetylene (525 mg, 4.37 mmol) was added to 1,1,1-tributyl-N,N-dimethylstannanamine (1.46 g, 4.37 mmol), and the mixture was stirred in a sealed vial at 50° C. for 2 hours. The mixture was cooled to ambient temperature, and the vial was stirred unsealed for 10 minutes. Benzyl azide (850 μL, 6.80 mmol) was added, and the vial was resealed and heated to 130° C. overnight. The mixture was purified by silica gel chromatography eluting with a gradient of 5-35% ethyl acetate in hexanes to afford the title compound. MS (ESI+) m/z 544.4 (M+H)+.

Aufarbeitung

  1. temperatureThe mixture was cooled to ambient temperature
  2. stirringthe vial was stirred unsealed for 10 minutes
  3. temperatureheated to 130° C. overnight
  4. customThe mixture was purified by silica gel chromatography
  5. washeluting with a gradient of 5-35% ethyl acetate in hexanes

Quellen und Nachweise

ORD-Eintrag
ord-d3fb472d1f604ee7b3a78794e7b2710c
Quelldatensatz
uspto-grants-2014_02
Patentnummer
US08648069B2

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