2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → [5-Bromo-4-(4-chlorobenzyl)-7-fluoro-1-oxo-1,2,3,4-tetrahydrocyclopenta[b]indol-3-yl]acetic acid methyl ester

HRID 2250539Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2250539
[Br:1][C:2]1[C:10]2[N:9]([CH2:11][C:12]3[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=3)[C:8]3[CH:19](CC(O)=O)[CH2:20][CH2:21][C:7]=3[C:6]=2[CH:5]=[C:4]([F:26])[CH:3]=1.[N+](=C)=[N-].C(C1C(=O)C(Cl)=C(Cl)C(=[O:35])C=1C#N)#N.C[CH2:45][O:46][C:47]([CH3:49])=[O:48]>C1COCC1.O.[Cl-].[Na+].O>[CH3:45][O:46][C:47](=[O:48])[CH2:49][CH:19]1[C:8]2[N:9]([CH2:11][C:12]3[CH:13]=[CH:14][C:15]([Cl:18])=[CH:16][CH:17]=3)[C:10]3[C:2]([Br:1])=[CH:3][C:4]([F:26])=[CH:5][C:6]=3[C:7]=2[C:21](=[O:35])[CH2:20]1

Komponenten

7

Edukt 4

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 8857Ethyl AcetateHCID 9550DiazomethaneHCID 18476687[4-(4-Chlorobenzyl)-7-fluoro-5-bromo-1,2,3,4-tetrahydrocyclopenta[B]indol-3-YL]acetic acid

Produkt 1

HCID 67021498[5-Bromo-4-(4-chlorobenzyl)-7-fluoro-1-oxo-1,2,3,4-tetrahydrocyclopenta[b]indol-3-yl]acetic acid methyl ester

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 21881883Oxolane--water (1/1)LösungsmittelHCID 57417360Sodium chloride; waterLösungsmittel

Versuchsvorschrift

The methyl ester of the compound of Example 1 step 5 (1.00 g, preapared by treating the corresponding acid with excess diazomethane) in 10 mL of a 9:1 THF/H2O solution was treated with 2.52 g of DDQ. The reaction mixture was allowed to stir at room temperature overnight. The reaction mixture at this time was poured into a separatory funnel containing EtOAc and brine. The combined organic layers were washed with water, brine, dried over anhydrous MgSO4 and concentrated. The resulting material was further purified by flash chromatography eluting with 30% EtOAc/hexane. The chromatography procedure was repeated an additional two times. 350 mg of the above ketone was obtained as a grey solid.

Aufarbeitung

  1. additionThe reaction mixture at this time was poured into a separatory funnel
  2. washThe combined organic layers were washed with water, brine
  3. dry with materialdried over anhydrous MgSO4
  4. concentrationconcentrated
  5. customThe resulting material was further purified by flash chromatography
  6. washeluting with 30% EtOAc/hexane

Quellen und Nachweise

ORD-Eintrag
ord-c6e0eb692e284508bc4321fdddf3d161
Quelldatensatz
uspto-grants-2008_01
Patentnummer
US07317036B2

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