Dimethylformamide → HCID 66893958, Verbindung

HRID 1161983Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1161983
I[C:2]1[C:10]2[O:9][CH:8]=[CH:7][C:6]=2[CH:5]=[C:4]([N+:11]([O-:13])=[O:12])[CH:3]=1.C([Sn](CCCC)(CCCC)[C:19]1[CH:24]=[CH:23][N:22]=[CH:21][CH:20]=1)CCC.CN(C=O)C.[OH-].[Na+]>[Cu]I.C(Cl)(Cl)Cl>[N+:11]([C:4]1[CH:3]=[C:2]([C:19]2[CH:24]=[CH:23][N:22]=[CH:21][CH:20]=2)[C:10]2[O:9][CH:8]=[CH:7][C:6]=2[CH:5]=1)([O-:13])=[O:12]

Komponenten

7

Edukt 4

HCID 6228DimethylformamideHCID 14798Sodium HydroxideHCID 27373184-(Tri-n-butylstannyl)pyridineHCID 218647647-Iodo-5-nitrobenzofuran

Produkt 1

HCID 66893958HCID 66893958, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 6212ChloroformLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

7-Iodo-5-nitrobenzofuran (2.00 g, 0.00692 mol), 4-tributylstannylpyridine (2.80 g, 0.00761 mol), copper(I)iodide (132 mg, 0.692 mmol) and dichlorobis(triphenylphosphine) palladium(II) (49 mg, 0.0692 mmol) were added to a 50 mL test tube followed by DMF (20 mL). The mixture was heated at 100° C. overnight in a StemBlock. After cooling to room temperature, aqueous sodium hydroxide (2 M; 4 mL) was added and the solution was stirred for 15 min. Chloroform (20 mL) was added and the mixture was filtered through Celite. The aqueous layer was then extracted with chloroform (3×) and the combined organic phases were evaporated. The residue was then triturated with ether and the precipitate was dried in vacuo overnight to yield a light brown solid. Yield: 686 mg (41%); HLPC (System A) purity=99%, m/z=241 (M+H)+, 1H NMR (270 MHz, DMSO-d6) δ ppm 7.33 (d, J=2.23 Hz, 1H) 7.98 (m, 2H) 8.38 (d, J=2.23 Hz, 1H) 8.50 (d, J=2.47 Hz, 1H) 8.75 (d, J=2.23 Hz, 1H) 8.79 (m, 2H).

Aufarbeitung

  1. temperatureAfter cooling to room temperature
  2. filtrationthe mixture was filtered through Celite
  3. extractionThe aqueous layer was then extracted with chloroform (3×)
  4. customthe combined organic phases were evaporated
  5. customThe residue was then triturated with ether
  6. customthe precipitate was dried in vacuo overnight
  7. customto yield a light brown solid

Quellen und Nachweise

ORD-Eintrag
ord-8dec0152ce674285a4af812e86495b03
Quelldatensatz
uspto-grants-2010_10
Patentnummer
US07820675B2

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