Propargyl alcohol → N-[(4-chlorophenyl)methyl]-7-ethyl-2-(3-hydroxyprop-1-ynyl)-4-oxo-thieno[2,3-b]pyridine-5-carboxamide

HRID 2299295Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2299295
[Cl:1][C:2]1[CH:24]=[CH:23][C:5]([CH2:6][NH:7][C:8]([C:10]2[C:11](=[O:22])[C:12]3[CH:20]=[C:19](I)[S:18][C:13]=3[N:14]([CH2:16][CH3:17])[CH:15]=2)=[O:9])=[CH:4][CH:3]=1.[CH2:25]([OH:28])[C:26]#[CH:27]>C(NCC)C.[Cu](I)I.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[Cl:1][C:2]1[CH:24]=[CH:23][C:5]([CH2:6][NH:7][C:8]([C:10]2[C:11](=[O:22])[C:12]3[CH:20]=[C:19]([C:27]#[C:26][CH2:25][OH:28])[S:18][C:13]=3[N:14]([CH2:16][CH3:17])[CH:15]=2)=[O:9])=[CH:4][CH:3]=1

Komponenten

6

Edukt 2

HCID 7859Propargyl alcoholHCID 9847660HCID 9847660, Verbindung

Produkt 1

HCID 6483693N-[(4-chlorophenyl)methyl]-7-ethyl-2-(3-hydroxyprop-1-ynyl)-4-oxo-thieno[2,3-b]pyridine-5-carboxamideAusbeute 70 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 83717Copper iodideKatalysatorHCID 178418476HCID 178418476, VerbindungKatalysatorHCID 8021DiethylamineLösungsmittel

Versuchsvorschrift

To a suspension of N-(4-chlorobenzyl)-7-ethyl-2-iodo4-oxo4,7-dihydro-thieno[2,3-b]pyridine-5-carboxamide (Example No. 12) (0.267 g) in diethylamine (14 mL) is added copper iodide (0.032 g) and Pd(PPh3)2Cl2 (0.009 g) followed by addition of propargyl alcohol (39 mL). The reaction is stirred at rt for 18 h. The diethylamine is removed in vacuo, and the resulting residue is partitioned between H2O (25 mL) and CH2Cl2 (25 mL). The organic layer is removed, and the aqueous layer is extracted with CH2Cl2 (3×25 mL). The combined organic layers are dried with MgSO4, filtered, and concentrated in vacuo. The resulting orange solid is purified by column chromatography (CH2Cl2:CH3OH, 98:2). Fractions homogeneous by TLC are combined and concentrated in vacuo to yield 0.158 g (70%) of the title compound as a yellow, crystalline solid.

Aufarbeitung

  1. customThe diethylamine is removed in vacuo
  2. customthe resulting residue is partitioned between H2O (25 mL) and CH2Cl2 (25 mL)
  3. customThe organic layer is removed
  4. extractionthe aqueous layer is extracted with CH2Cl2 (3×25 mL)
  5. dry with materialThe combined organic layers are dried with MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe resulting orange solid is purified by column chromatography (CH2Cl2:CH3OH, 98:2)
  9. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-ee0e2fa15e864cbba27844d5a2aa8a04
Quelldatensatz
uspto-grants-2002_12
Patentnummer
US06495683B2

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