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Potassium Carbonate → tert-butyl 5,7-dichloro-2-(4-methoxybenzyl)-3-oxo-2',3'-dihydro-1'H-spiro[isoindoline-1,4'-pyridine]-1'-carboxylate

HRID 390141
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 390141
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH:12]=[C:11]([N:14]([C:24](=[O:34])[C:25]2[CH:30]=[C:29]([Cl:31])[CH:28]=[C:27]([Cl:32])[C:26]=2I)[CH2:15][C:16]2[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C([O-])([O-])=O.[K+].[K+]>C(#N)C.[N+](CCCC)(CCCC)(CCCC)CCCC.[Br-].CC([O-])=O.CC([O-])=O.[Pd+2]>[Cl:32][C:27]1[CH:26]=[C:25]2[C:30](=[C:29]([Cl:31])[CH:28]=1)[C:11]1([CH:12]=[CH:13][N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[CH2:9][CH2:10]1)[N:14]([CH2:15][C:16]1[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=1)[C:24]2=[O:34]
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Komponenten

7

Edukt 3

HCID 11430Potassium CarbonateHCID 11776TriphenylphosphineHCID 582957824-[(3,5-Dichloro-2-iodo-benzoyl)-(4-methoxy-benzyl)-amino]-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester

Produkt 1

HCID 58295806tert-butyl 5,7-dichloro-2-(4-methoxybenzyl)-3-oxo-2',3'-dihydro-1'H-spiro[isoindoline-1,4'-pyridine]-1'-carboxylateAusbeute 48 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 74236Tetrabutylammonium BromideKatalysatorHCID 167845palladium(II) acetateKatalysatorHCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

4-[(3,5-Dichloro-2-iodo-benzoyl)-(4-methoxy-benzyl)-amino]-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester (9.0 g, 15 mmol) was dissolved in 100 mL of acetonitrile in a three flask fitted with a condenser and the mixture was sparged with N2 for 1 h. The flask was quickly opened and Pd(OAc)2 (336 mg, 1.5 mmol), PPh3 (786 mg, 3.0 mmol), K2CO3 (4.14 g, 30 mmol) and nBu4NBr (4.82 g, 15 mmol) was added. The mixture was heated to reflux overnight. After this time, the iodide was consumed and the mixture was cooled to rt and evaporated. The residue was taken up with EtOAc/H2O and the layers were separated. The organic layer was washed with brine, dried and concentrated to give the crude product. It was purified by column chromatography (PE:EtOAc=10:1) to give tert-butyl 5,7-dichloro-2-(4-methoxybenzyl)-3-oxo-2′,3′-dihydro-1′H-spiro[isoindoline-1,4′-pyridine]-1′-carboxylate (3.5 g, 48%). 1H NMR (CDCl3): 1.52 (s, 9H), 1.63 (s, 1H), 1.78 (m, 1H), 2.71 (m, 1H), 3.04 (m, 1H), 3.78 (s, 3H), 3.97 (m, 1H), 4.25 (m, 1H), 4.46 (m, 1H), 5.02 (m, 1H), 6.82 (m, 2H), 7.18 (m, 2H), 7.52 (s, 1H), 7.81 (s, 1H).

Aufarbeitung

  1. customfitted with a condenser
  2. customthe mixture was sparged with N2 for 1 h
  3. temperatureThe mixture was heated
  4. temperatureto reflux overnight
  5. customAfter this time, the iodide was consumed
  6. customevaporated
  7. customthe layers were separated
  8. washThe organic layer was washed with brine
  9. customdried
  10. concentrationconcentrated
  11. customto give the crude product
  12. customIt was purified by column chromatography (PE:EtOAc=10:1)

Quellen und Nachweise

ORD-Eintrag
ord-960480494c0c44d4a03db1227b21edc6
Quelldatensatz
uspto-grants-2013_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08383629B2

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