Phosphorus oxychloride → ethyl-7-chloro-2-methyl-1H-pyrrolo[3,2-b]pyridine-3-carboxylate

HRID 2410935Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2410935
O[C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[C:8]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[C:9]([CH3:11])[NH:10][C:3]=12.O=P(Cl)(Cl)[Cl:19]>C(#N)C>[CH2:15]([O:14][C:12]([C:8]1[C:4]2=[N:5][CH:6]=[CH:7][C:2]([Cl:19])=[C:3]2[NH:10][C:9]=1[CH3:11])=[O:13])[CH3:16]

Komponenten

4

Edukt 2

HCID 24813Phosphorus oxychlorideHCID 178469265HCID 178469265, Verbindung

Produkt 1

HCID 67774803ethyl-7-chloro-2-methyl-1H-pyrrolo[3,2-b]pyridine-3-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

Ethyl 7-hydroxy-2-methyl-1H-pyrrolo[3,2-b]pyridine-3-carboxylate (44.0 g, 0.20 mol) is suspended in dry acetonitrile (400 mL). After addition of POCl3 (47 mL, 0.50 mol) the stirred reaction mixture is heated to reflux for 4 hours. The volatiles are removed under reduced pressure. The residue is suspended in ice-cold water (500 mL) and carefully neutralized to pH 8 by dropwise addition of 6N NaOH. Stirring is continued at ambient temperature over night. The pH is readjusted to 8, the product is filtered, washed with several small portions of water and dried in vacuum at 50° C. for 24 hours to yield the title compound as off-white solid.

Aufarbeitung

  1. customthe stirred reaction mixture
  2. temperatureis heated
  3. temperatureto reflux for 4 hours
  4. customThe volatiles are removed under reduced pressure
  5. additioncarefully neutralized to pH 8 by dropwise addition of 6N NaOH
  6. waitis continued at ambient temperature over night
  7. filtrationthe product is filtered
  8. washwashed with several small portions of water
  9. customdried in vacuum at 50° C. for 24 hours

Quellen und Nachweise

ORD-Eintrag
ord-166ec474213f4b688f1929c4f34a363c
Quelldatensatz
uspto-grants-2014_08
Patentnummer
US08816085B2

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