Triethylamine → 3-[3-(2-Methoxy-ethoxy)-phenylethynyl]-5-nitro-pyridin-2-ylamine

HRID 506595Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 506595
[CH3:1][O:2][CH2:3][CH2:4][O:5][C:6]1[CH:7]=[C:8]([C:12]#[CH:13])[CH:9]=[CH:10][CH:11]=1.C(N(CC)CC)C.[NH2:21][C:22]1[C:27](Br)=[CH:26][C:25]([N+:29]([O-:31])=[O:30])=[CH:24][N:23]=1>O1CCCC1.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.[Cu]I>[CH3:1][O:2][CH2:3][CH2:4][O:5][C:6]1[CH:7]=[C:8]([C:12]#[C:13][C:27]2[C:22]([NH2:21])=[N:23][CH:24]=[C:25]([N+:29]([O-:31])=[O:30])[CH:26]=2)[CH:9]=[CH:10][CH:11]=1

Komponenten

7

Edukt 3

HCID 8471TriethylamineHCID 27344122-Amino-3-bromo-5-nitropyridineHCID 714077821-Ethynyl-3-(2-methoxyethoxy)benzene

Produkt 1

HCID 684671423-[3-(2-Methoxy-ethoxy)-phenylethynyl]-5-nitro-pyridin-2-ylamineAusbeute 74,5 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 178418476HCID 178418476, VerbindungKatalysatorHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

3-(2-Methoxy-ethoxy)-phenylacetylene (6.3 g, 36 mmol) was added to a solution of triethylamine (1.92 mL, 14 mmol), 2-amino-3-bromo-5-nitropyridine (4 g, 18 mmol), PdCl2(PPh3)2 (966 mg, 1.38 mmol) and CuI (262 mg, 1.38 mmol) in anhydrous tetrahydrofuran (80 mL) in the dark. The mixture was stirred at room temperature for 48 hours then concentrated in vacuo and dissolved in dichloromethane (150 mL). The organic solution was washed with water (25 mL), dried over MgSO4, filtered and concentrated in vacuo to 20% of its original volume and heptane (20 mL) was then added. The resultant yellow solid was filtered and dried to give 3-[3-(2-methoxy-ethoxy)-phenylethynyl]-5-nitro-pyridin-2-ylamine (4.2 g, 74% yield).

Aufarbeitung

  1. concentrationthen concentrated in vacuo
  2. dissolutiondissolved in dichloromethane (150 mL)
  3. washThe organic solution was washed with water (25 mL)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo to 20% of its original volume and heptane (20 mL)
  7. additionwas then added
  8. filtrationThe resultant yellow solid was filtered
  9. customdried

Quellen und Nachweise

ORD-Eintrag
ord-410ba799084844a6af81776bea0d502e
Quelldatensatz
uspto-grants-2010_08
Patentnummer
US07786113B2

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