Hydrochloric Acid → 2-Chloro-4-hydroxy-3-(4-bromophenyl)-6-oxo-6,7-dihydrothieno[2,3-b]pyridine-5-carbonitrile

HRID 1244094Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1244094
[H-].[Na+].C(O[C:6]([C:8]1[C:12]([C:13]2[CH:18]=[CH:17][C:16]([Br:19])=[CH:15][CH:14]=2)=[C:11]([Cl:20])[S:10][C:9]=1[NH:21][C:22](=[O:26])[CH2:23][C:24]#[N:25])=[O:7])C.Cl>O1CCCC1>[Cl:20][C:11]1[S:10][C:9]2[NH:21][C:22](=[O:26])[C:23]([C:24]#[N:25])=[C:6]([OH:7])[C:8]=2[C:12]=1[C:13]1[CH:14]=[CH:15][C:16]([Br:19])=[CH:17][CH:18]=1

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 696073704-(4-Bromophenyl)-5-chloro-2-(2-cyano-acetylamino)-thiophene-3-carboxylic acid ethyl ester

Produkt 1

HCID 546898652-Chloro-4-hydroxy-3-(4-bromophenyl)-6-oxo-6,7-dihydrothieno[2,3-b]pyridine-5-carbonitrile

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

To a suspension of NaH (1.33 g, 33.2 mmol, 60% dispersion in mineral oil) in tetrahydrofuran (60 mL) at room temperature was added a solution of 4-(4-bromophenyl)-5-chloro-2-(2-cyano-acetylamino)-thiophene-3-carboxylic acid ethyl ester (5.26 g, 12.3 mmol) in tetrahydrofuran (60 mL) over 15 minutes. The reaction was stirred at room temperature for 12 h, and 1 N HCl was added (15 mL). The reaction was then concentrated under reduced pressure, and the resulting solid was triturated with water (15 mL) and diethyl ether (20 mL) to provide the titled compound. MS (APCI) m/e 381 (M−H)−.

Aufarbeitung

  1. concentrationThe reaction was then concentrated under reduced pressure
  2. customthe resulting solid was triturated with water (15 mL) and diethyl ether (20 mL)

Quellen und Nachweise

ORD-Eintrag
ord-a597eb01d90f443eb10e8a12ebdcfaeb
Quelldatensatz
uspto-grants-2006_10
Patentnummer
US07119205B2

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