Sodium Carbonate → HCID 57774343, Verbindung

HRID 1786763Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1786763
[Cl:1][C:2]1[CH:3]=[C:4](I)[C:5]([NH2:8])=[N:6][CH:7]=1.[CH2:10]([Si:12]([C:17]#[CH:18])([CH2:15][CH3:16])[CH2:13][CH3:14])[CH3:11].[Cl-].[Li+].C([O-])([O-])=O.[Na+].[Na+]>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[C:4]2[CH:11]=[C:10]([Si:12]([CH2:17][CH3:18])([CH2:15][CH3:16])[CH2:13][CH3:14])[NH:8][C:5]2=[N:6][CH:7]=1

Komponenten

6

Edukt 4

HCID 10340Sodium CarbonateHCID 433294Lithium ChlorideHCID 637947(Triethylsilyl)acetyleneHCID 110760102-Amino-5-chloro-3-iodopyridine

Produkt 1

HCID 57774343HCID 57774343, VerbindungAusbeute 44 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

A mixture of 40 (9.5 g, 37.3 mmol) was dissolved in 320 mL of DMF and triethylsilylacetylene (20 mL, 112 mmol), Pd2Cl2 (dppf)2 (1.52 g, 1.9 mmol), lithium chloride (1.58 g, 37.3 mmol) and 2M Na2CO3 (7.9 mL, 74.7 mL) were added and the mixture was stirred and refluxed at 90° C. for 15 h under nitrogen. Diluted with ethyl acetate-ether mixture (1:1) and the organic phase washed with water and brine then dried (Na2SO4) and concentrated in vacuo. The residue was subjected to flash chromatography (20% EtOAc/80% hexanes) to give 4.37 g (44%) of the desired product 41. 1H NMR (500 MHz, CDCl3) 9.4 (bs, 1H), 8.2 (s, 1H), 7.9 (s, 1H), 6.6 (s, 1H), 0.9 (t, 9H), 0.75 (q, 6H).

Aufarbeitung

  1. washthe organic phase washed with water and brine
  2. dry with materialthen dried (Na2SO4)
  3. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-e1735d1e75c74ebb9fa2d2666c3cd572
Quelldatensatz
uspto-grants-2009_03
Patentnummer
US07507826B2

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