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Phosphorus oxychloride → Ethyl 4-chloro-1-(4-methoxybenzyl)-1H-pyrazolo[3,4-b]pyridine-5-carboxylate

HRID 1499480
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1499480
[CH3:1][O:2][C:3]1[CH:24]=[CH:23][C:6]([CH2:7][N:8]2[C:12]3[NH:13][CH:14]=[C:15]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[C:16](=O)[C:11]=3[CH:10]=[N:9]2)=[CH:5][CH:4]=1.O=P(Cl)(Cl)[Cl:27]>ClCCCl>[Cl:27][C:16]1[C:15]([C:18]([O:20][CH2:21][CH3:22])=[O:19])=[CH:14][N:13]=[C:12]2[N:8]([CH2:7][C:6]3[CH:23]=[CH:24][C:3]([O:2][CH3:1])=[CH:4][CH:5]=3)[N:9]=[CH:10][C:11]=12
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Komponenten

4

Edukt 2

HCID 24813Phosphorus oxychlorideHCID 135741690ethyl 4-hydroxy-1-(4-methoxybenzyl)-1H-pyrazolo[3,4-b]pyridine-5-carboxylate

Produkt 1

HCID 53665897Ethyl 4-chloro-1-(4-methoxybenzyl)-1H-pyrazolo[3,4-b]pyridine-5-carboxylateAusbeute 95 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 111,2-DichloroethaneLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

To a solution of ethyl 1-(4-methoxybenzyl)-4-oxo-4,7-dihydro-1H-pyrazolo[3,4-b]pyridine-5-carboxylate (4.0 g, 13 mmol) in 1,2-dichloroethane (9.8 mL) was added POCl3 (2.4 mL, 26 mmol). The resulting mixture was heated at 90° C. for 3 h. After cooling, the most volatile were removed by vacuum, and the residue was diluted with EtOAc and washed with aq. Na2CO3 solution. The organic layer was washed water and brine, dried and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel using CombiFlash® apparatus, eluting with 10 to 60% EtOAc in hexanes, to give the sub-title compound (3.9 g, 95%). LCMS calc. for C17H17ClN3O3 (M+H)+: m/z=346.1. Found: 346.1.

Aufarbeitung

  1. temperatureAfter cooling
  2. customthe most volatile were removed by vacuum
  3. additionthe residue was diluted with EtOAc
  4. washwashed with aq. Na2CO3 solution
  5. washThe organic layer was washed water and brine
  6. customdried
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by column chromatography on silica gel using CombiFlash® apparatus
  9. washeluting with 10 to 60% EtOAc in hexanes

Quellen und Nachweise

ORD-Eintrag
ord-48d36b036dc54d5f9c69eabb2b17f286
Quelldatensatz
uspto-grants-2015_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09200004B2

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