Sodium Carbonate → 5-(2-Oxopyrrolidin-1-yl)-biphenyl-3-carboxylic Acid Methyl Ester

HRID 1612436Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1612436
[CH3:1][O:2][C:3](=[O:17])[C:4]1[CH:9]=[C:8]([N:10]2[CH2:14][CH2:13][CH2:12][C:11]2=[O:15])[CH:7]=[C:6](Br)[CH:5]=1.C([O-])([O-])=O.[Na+].[Na+].[C:24]1(B(O)O)[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>COCCOC.CC([O-])=O.CC([O-])=O.[Pd+2]>[CH3:1][O:2][C:3]([C:4]1[CH:5]=[C:6]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH:7]=[C:8]([N:10]2[CH2:14][CH2:13][CH2:12][C:11]2=[O:15])[CH:9]=1)=[O:17]

Komponenten

6

Edukt 3

HCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 22253055Methyl 3-bromo-5-(2-oxopyrrolidin-1-yl)benzoate

Produkt 1

HCID 695897705-(2-Oxopyrrolidin-1-yl)-biphenyl-3-carboxylic Acid Methyl EsterAusbeute 33,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 167845palladium(II) acetateKatalysatorHCID 80711,2-DimethoxyethaneLösungsmittel

Reaktionsbedingungen

Temperatur
85 °C

Versuchsvorschrift

To 3-bromo-5-(2-oxopyrrolidin-1-yl)benzoic acid methyl ester (D9) (70 mg, 0.235 mmol) in DME (2 ml) was added Na2CO3 (290 μl, 2M, 0.588 mmol), benzeneboronic acid (29 mg, 0.235 mmol) and Pd(OAc)2 (3 mg, 0.013 mmol). The mixture was stirred at 85° C. for 2 days. The reaction mixture was cooled down, filtrated through celite and evaporated in vacuo. The product was purified by column chromatography (PE:EtOAc=3:1) which yielded D10 (23 mg).

Aufarbeitung

  1. temperatureThe reaction mixture was cooled down
  2. filtrationfiltrated through celite
  3. customevaporated in vacuo
  4. customThe product was purified by column chromatography (PE:EtOAc=3:1) which

Quellen und Nachweise

ORD-Eintrag
ord-95a34c1f03144faaa63971fadbafdd6d
Quelldatensatz
uspto-grants-2006_01
Patentnummer
US06992103B2

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