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Potassium Carbonate → 6-(2'-Formyl-biphenyl-4-yl)-1-(4-methoxy-phenyl)-7-oxo-4,5,6,7-tetrahydro-1H-pyrazolo[3,4-c]pyridine-3-carboxylic acid ethyl ester

HRID 896811
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 896811
[CH2:1]([O:3][C:4]([C:6]1[C:14]2[CH2:13][CH2:12][N:11]([C:15]3[CH:20]=[CH:19][C:18](I)=[CH:17][CH:16]=3)[C:10](=[O:22])[C:9]=2[N:8]([C:23]2[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[CH:25][CH:24]=2)[N:7]=1)=[O:5])[CH3:2].[CH:31]([C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=1B(O)O)=[O:32].C([O-])([O-])=O.[K+].[K+]>C1(C)C=CC=CC=1.C(O)C.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH2:1]([O:3][C:4]([C:6]1[C:14]2[CH2:13][CH2:12][N:11]([C:15]3[CH:20]=[CH:19][C:18]([C:34]4[CH:35]=[CH:36][CH:37]=[CH:38][C:33]=4[CH:31]=[O:32])=[CH:17][CH:16]=3)[C:10](=[O:22])[C:9]=2[N:8]([C:23]2[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[CH:25][CH:24]=2)[N:7]=1)=[O:5])[CH3:2]
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Komponenten

8

Edukt 3

HCID 11430Potassium CarbonateHCID 2921892-Formylphenylboronic acidHCID 22240493Ethyl 6-(4-iodophenyl)-1-(4-methoxyphenyl)-7-oxo-4,5-dihydropyrazolo[3,4-c]pyridine-3-carboxylate

Produkt 1

HCID 223185346-(2'-Formyl-biphenyl-4-yl)-1-(4-methoxy-phenyl)-7-oxo-4,5,6,7-tetrahydro-1H-pyrazolo[3,4-c]pyridine-3-carboxylic acid ethyl esterAusbeute 84 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 178418397HCID 178418397, VerbindungKatalysator
HCID 702EthanolLösungsmittel
HCID 962WaterLösungsmittel2×
HCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
7.5 °C

Versuchsvorschrift

Method A. A suspension 1-(4-methoxy-phenyl)-6-(4-iodo-phenyl)-7-oxo-4,5,6,7-tetrahydro-1H-pyrazolo[3,4-c]pyridine-3-carboxylic acid ethyl ester (55, 2.0 g, 3.87 mmol), 2-formylphenylboronic acid (13, 870 mg, 5.81 mmol, 1.5 equiv), and K2CO3 (1.60 g, 11.6 mmol, 3.0 equiv) in toluene (18 mL), ethanol (6 mL) and H2O (6 mL) at room temperature was degassed three times under a steady nitrogen stream before being treated with Pd(PPh3)4 (22 mg, 0.02 mmol, 5% equiv) at room temperature under N2. The reaction mixture was subsequently degassed three times again before being warmed to reflux for 12 h. When HPLC showed the Suzuki coupling reaction was complete, the reaction mixture was cooled down to 5-10° C. before being treated with water (20 mL) at 5-10° C. with good stirring. The mixture was stirred for an additional 1 h at 5-10° C. before the solids were collected by filtration. The wet cake was then thoroughly washed with water (2×30 mL) and 30% EtOAc/hexane (2×20 mL), dried in vacuo at 40-45° C. for 12 h to afford the crude desired 6-(2′-formyl-biphenyl-4-yl)-1-(4-methoxy-phenyl)-7-oxo-4,5,6,7-tetrahydro-1H-pyrazolo[3,4-c]pyridine-3-carboxylic acid ethyl ester (56, 1.61 g, 1.915 g theoretical, 84%) as off-white solids, which was found to be pure enough to do the following reaction without further purification. For 56, CIMS m/z 496 (M++H, C29H25N3O5).

Aufarbeitung

  1. customThe reaction mixture was subsequently degassed three times again
  2. temperaturebefore being warmed
  3. temperatureto reflux for 12 h
  4. customthe Suzuki coupling reaction
  5. filtrationwere collected by filtration
  6. washThe wet cake was then thoroughly washed with water (2×30 mL) and 30% EtOAc/hexane (2×20 mL)
  7. customdried in vacuo at 40-45° C. for 12 h

Quellen und Nachweise

ORD-Eintrag
ord-0acd41158f914fa6ba4cfa12c2a47d31
Quelldatensatz
uspto-grants-2005_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06919451B2

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