4-Bromobenzyl bromide → HCID 19041639, Verbindung

HRID 1683993

Reaktionsgleichung

Reaktionsgleichung von HRID 1683993
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7]([CH3:12])=[C:6]2[CH2:13][C:14]([O:16][CH3:17])=[O:15].[CH3:18][Si]([N-][Si](C)(C)C)(C)C.[K+].[Br:28][C:29]1[CH:36]=[CH:35][C:32]([CH2:33]Br)=[CH:31][CH:30]=1>C1COCC1.C1(C)C=CC=CC=1.CN(P(N(C)C)(N(C)C)=O)C>[Br:28][C:29]1[CH:36]=[CH:35][C:32]([CH2:33][N:8]2[C:9]3[C:5](=[CH:4][C:3]([O:2][CH3:1])=[CH:11][CH:10]=3)[C:6]([CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])=[C:7]2[CH3:12])=[CH:31][CH:30]=1

Komponenten

7

Edukt 3

HCID 685274-Bromobenzyl bromideHCID 82067methyl 2-(5-methoxy-2-methyl-1H-indol-3-yl)acetateHCID 3251421Potassium bis(trimethylsilyl)amide

Produkt 1

HCID 19041639HCID 19041639, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 1140TolueneLösungsmittelHCID 8028TetrahydrofuranLösungsmittelHCID 12679HexamethylphosphoramideLösungsmittel

Versuchsvorschrift

To the ethyl ester from Example 7, Step 1 (2.00 g, 8.10 mmol) dissolved in THF (40.0 mL) was added at -78° C. a 0.5M solution of KHMDS (16.0 mL, 8.10 mmol) in toluene and HMPA (200 μL). After a period of 10 min, 4-bromobenzyl bromide was added to the resulting mixture. The reaction mixture was brought to room temperature, quenched by the addition of 25% aqueous NH4OAc solution, extracted with EtOAc, dried over Na2SO4 and evaporated in vacuo. The title product was purified by flash chromotography (15% to 20% EtOAc in hexane) (1.5 g).

Aufarbeitung

  1. customwas brought to room temperature
  2. customquenched by the addition of 25% aqueous NH4OAc solution
  3. extractionextracted with EtOAc
  4. dry with materialdried over Na2SO4
  5. customevaporated in vacuo
  6. customThe title product was purified by flash chromotography (15% to 20% EtOAc in hexane) (1.5 g)

Quellen und Nachweise

ORD-Eintrag
ord-c7b0d7a0906f4359a7b3da0bd41fcd43
Quelldatensatz
uspto-grants-1997_06
Patentnummer
US05639780

Verknüpfte Notizen

Wird geladen…