Sodium hydride → HCID 86648959, Verbindung

HRID 449918

Reaktionsgleichung

Reaktionsgleichung von HRID 449918
[Cl:1][C:2]1[CH:10]=[C:9]([I:11])[CH:8]=[C:7]([Cl:12])[C:3]=1[C:4](Cl)=[O:5].[H-].[Na+].[Br:15][C:16]1[CH:21]=[C:20]([NH2:22])[CH:19]=[CH:18][N:17]=1>CN(C=O)C.C(OCC)(=O)C>[Br:15][C:16]1[CH:21]=[C:20]([NH:22][C:4](=[O:5])[C:3]2[C:2]([Cl:1])=[CH:10][C:9]([I:11])=[CH:8][C:7]=2[Cl:12])[CH:19]=[CH:18][N:17]=1

Komponenten

6

Edukt 3

HCID 24758Sodium hydrideHCID 3464554-Amino-2-bromopyridineHCID 866489582,6-Dichloro-4-iodobenzoyl chloride

Produkt 1

HCID 86648959HCID 86648959, VerbindungAusbeute 40,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
25 °C

Versuchsvorschrift

To a cooled (0° C.) solution of 2,6-dichloro-4-iodobenzoyl chloride (70 mg, 0.21 mmol) in DMF (2 mL) was added NaH (17 mg, 0.42 mmol). The mixture was stirred for 10 minutes and then 2-bromopyridin-4-amine (40 mg, 0.23 mmol) was added. The resulting mixture was slowly warmed to 25° C., diluted with ethyl acetate (10 mL), quenched with water (1 mL), washed with saturated Na2CO3 and water, dried over Na2SO4, and concentrated under reduced pressure. The residue was purified by silica-gel chromatography (Pet Ether/EtOAc=20:1 to 3:1) to afford N-(2-bromopyridin-4-yl)-2,6-dichloro-4-iodobenzamide (40 mg, 40% yield). LCMS (ESI) m/z: 470.9 [M+H+].

Aufarbeitung

  1. customquenched with water (1 mL)
  2. washwashed with saturated Na2CO3 and water
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica-gel chromatography (Pet Ether/EtOAc=20:1 to 3:1)

Quellen und Nachweise

ORD-Eintrag
ord-ddc5ea3b64ed4938a33ec0ef9afda5ed
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08486950B2

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