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3-Butyn-1-OL → HCID 10309452, Verbindung

HRID 1814891
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1814891
Br[C:2]1[O:23][C:5]2[N:6]([CH3:22])[CH:7]=[C:8]([C:11]([NH:13][CH2:14][C:15]3[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=3)=[O:12])[C:9](=[O:10])[C:4]=2[CH:3]=1.[CH2:24]([OH:28])[CH2:25][C:26]#[CH:27]>C(N(CC)CC)C.CN(C=O)C.[Cu]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:21][C:18]1[CH:19]=[CH:20][C:15]([CH2:14][NH:13][C:11]([C:8]2[C:9](=[O:10])[C:4]3[CH:3]=[C:2]([C:27]#[C:26][CH2:25][CH2:24][OH:28])[O:23][C:5]=3[N:6]([CH3:22])[CH:7]=2)=[O:12])=[CH:16][CH:17]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 2

HCID 135663-Butyn-1-OLHCID 10237594HCID 10237594, Verbindung

Produkt 1

HCID 10309452HCID 10309452, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 178418476HCID 178418476, VerbindungKatalysator
HCID 6228
Dimethylformamide
Lösungsmittel
HCID 8471TriethylamineLösungsmittel

Versuchsvorschrift

2-Bromo-N-(4-chlorobenzyl)-7-methyl-4-oxo-4,7-dihydrofuro[2,3-b]-pyridine-5-carboxamide (Example 79, 0.100 g) was suspended in a mixture of triethylamine (2.5 mL) and DMF (0.5 mL). CuI (0.006 g), Pd(PPh3)2Cl2 (0.017 g), and then 3-butyn-1-ol (0.038 mL) were added. The mixture was stirred at room temperature for 30 min and then was partitioned between CH2Cl2 (10 mL) and water (10 mL). The aqueous layer was separated and was extracted with CH2Cl2 (3×10 mL). The combined organic layers were washed with a sat. aq. ammonium chloride solution (10 mL), dried (MgSO4), filtered, and concentrated in vacuo. The resulting solid was purified by column chromatography (CH2Cl2/methanol; 99/1, 98/2) followed by recrystallization from ethyl acetate to yield 0.035 g of the title compound as a pale yellow solid. Physical characteristics. M.p. 242-243° C. (dec); 1H NMR (400 MHz, DMSO-d6) δ 10.51, 8.59, 7.41-7.32, 7.21, 5.01, 4.55, 3.92, 3.61, 2.67; MS (ESI+) m/z 385 (,M+H)+.

Aufarbeitung

  1. customwas partitioned between CH2Cl2 (10 mL) and water (10 mL)
  2. customThe aqueous layer was separated
  3. extractionwas extracted with CH2Cl2 (3×10 mL)
  4. washThe combined organic layers were washed with a sat. aq. ammonium chloride solution (10 mL)
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe resulting solid was purified by column chromatography (CH2Cl2/methanol; 99/1, 98/2)
  9. customfollowed by recrystallization from ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-8a73ee19d06b45d999a9999cbd5b71e3
Quelldatensatz
uspto-grants-2005_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06878705B2

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