Formic Acid → (+/-)-7-Chloro-1,3,4,10b-tetrahydropyrido[2,1-a]isoindole-2,6-dione

HRID 2287348Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2287348
Br[C:2]1[CH:16]=[CH:15][CH:14]=[C:13]([Cl:17])[C:3]=1[C:4]([N:6]1[CH:11]=[CH:10][C:9](=[O:12])[CH2:8][CH2:7]1)=[O:5].C(N(CC)CC)C.C(O)=O>CN(C=O)C>[Cl:17][C:13]1[CH:14]=[CH:15][CH:16]=[C:2]2[C:3]=1[C:4](=[O:5])[N:6]1[CH2:11][CH2:10][C:9](=[O:12])[CH2:8][CH:7]12

Komponenten

5

Edukt 3

HCID 284Formic AcidHCID 8471TriethylamineHCID 22008838HCID 22008838, Verbindung

Produkt 1

HCID 22008819(+/-)-7-Chloro-1,3,4,10b-tetrahydropyrido[2,1-a]isoindole-2,6-dioneAusbeute 31,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

A mixture of 1-(2-bromo-6-chlorobenzoyl)-2,3-dihydro-4-pyridinone (Preparation 3) (300 mg, 0.954 mmol), triethylamine (0.39 mmol, 0.54 ml), formic acid (0.05 ml, 1.3 mmol) and di(triphenylphosphine)diacetoxypalladium (47 mg, 0.063 mmol) in DMF (3 ml) was heated to 80° C. for 2 h. The cooled solution was filtered through celite, diluted with water, extracted twice with ethyl acetate, the extracts dried over sodium sulphate and evaporated. The residue was purified by flash column chromatography on silica eluting with 50% ethyl acetate in hexane to yield the title compound as a colourless oil (70 mg). MS (+CI) m /z 235/237 [M+H]+.

Aufarbeitung

  1. filtrationThe cooled solution was filtered through celite
  2. additiondiluted with water
  3. extractionextracted twice with ethyl acetate
  4. dry with materialthe extracts dried over sodium sulphate
  5. customevaporated
  6. customThe residue was purified by flash column chromatography on silica eluting with 50% ethyl acetate in hexane

Quellen und Nachweise

ORD-Eintrag
ord-cc8251cae7244dcebea2b7876866957d
Quelldatensatz
uspto-grants-2000_07
Patentnummer
US06083952

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