4,5-Diphenyl-1-tritylimidazole → HCID 68815696, Verbindung

HRID 2104960Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2104960
[C:1]1([C:7]2[N:8]=[CH:9][N:10]([C:18]([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[C:11]=2[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Li]CCCC.[CH2:42]([O:44][C:45]1[CH:46]=[C:47]([O:62][CH:63]([CH3:65])[CH3:64])[C:48]([F:61])=[C:49]([CH:60]=1)/[CH:50]=[N:51]/[C:52]1[CH:59]=[CH:58][C:55]([C:56]#[N:57])=[CH:54][CH:53]=1)[CH3:43]>C1COCC1>[C:1]1([C:7]2[N:8]=[C:9]([N:51]([CH2:50][C:49]3[CH:60]=[C:45]([O:44][CH2:42][CH3:43])[CH:46]=[C:47]([O:62][CH:63]([CH3:65])[CH3:64])[C:48]=3[F:61])[C:52]3[CH:59]=[CH:58][C:55]([C:56]#[N:57])=[CH:54][CH:53]=3)[N:10]([C:18]([C:31]3[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=3)([C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=3)[C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=3)[C:11]=2[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Komponenten

5

Edukt 3

HCID 41804394,5-Diphenyl-1-tritylimidazoleHCID 178418339ButyllithiumHCID 178466720HCID 178466720, Verbindung

Produkt 1

HCID 68815696HCID 68815696, VerbindungAusbeute 56,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a solution of Intermediate 19.1 (100 mg, 0.216 mmol) in 3 mL THF at 0° C., was added BuLi (1.4 M in THF, 170 μL, 0.238 mmol). The mixture was stirred at 0° C. for 20 min, then a solution of Intermediate 7.3 (70.5 mg, 0.216 mmol) in 0.5 mL THF was added dropwise. The mixture was stirred at rt for 30 min, then was quenched with sat. NH4Cl. The mixture was diluted with EtOAc, washed with H2O and brine, dried (Na2SO4) and concentrated. The crude product was purified by flash chromatography (0 to 30% EtOAc/hexanes gradient) to afford 96 mg of Intermediate 19.2 as a white solid.

Aufarbeitung

  1. stirringThe mixture was stirred at rt for 30 min
  2. customwas quenched with sat. NH4Cl
  3. additionThe mixture was diluted with EtOAc
  4. washwashed with H2O and brine
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated
  7. customThe crude product was purified by flash chromatography (0 to 30% EtOAc/hexanes gradient)

Quellen und Nachweise

ORD-Eintrag
ord-55cf5ad1fde8488695dab65471f7ce26
Quelldatensatz
uspto-grants-2009_08
Patentnummer
US07576098B2

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