Dimethylformamide → Imidazo[1,2-a]pyridine-7-carbonitrile, 3-iodo-

HRID 246241Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 246241
[N:1]1[CH:2]=[CH:3][N:4]2[CH:9]=[CH:8][C:7]([C:10]#[N:11])=[CH:6][C:5]=12.[I:12]N1C(=O)CCC1=O.CN(C=O)C>C(OCC)(=O)C.C1COCC1.S([O-])([O-])(=O)=S.[Na+].[Na+]>[I:12][C:3]1[N:4]2[CH:9]=[CH:8][C:7]([C:10]#[N:11])=[CH:6][C:5]2=[N:1][CH:2]=1

Komponenten

7

Edukt 3

HCID 6228DimethylformamideHCID 120273N-IodosuccinimideHCID 55267408Imidazo(1,2-a)pyridine-7-carbonitrile

Produkt 1

HCID 59320953Imidazo[1,2-a]pyridine-7-carbonitrile, 3-iodo-

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittelHCID 24477Sodium ThiosulfateLösungsmittel

Versuchsvorschrift

In a 50 mL round-bottomed flask, imidazo[1,2-a]pyridine-7-carbonitrile (1.1 g, 7.68 mmol) and N-iodosuccinimide (2.07 g, 9.22 mmol) were combined with DMF (50 ml) to give a colorless solution. The reaction mixture kept at 20° C. and stirred for 2 h. The reaction mixture was diluted with ethyl acetate (150 ml), THF (50 ml) and 300 ml of 5% sodium thiosulfate and well shaken. The aqueous layer was back-extracted with ethyl acetate (1×100 mL). The organic layers were combined, washed with water, brine, dried (MgSO4) and evaporated. The crude material was purified by flash chromatography (silica gel, 60% to 80% ethyl acetate/hexanes) to give 3-iodo-imidazo[1,2-a]pyridine-7-carbonitrile. 1H NMR (300 MHz, DMSO-d6) δ: 8.52 (d, 1H) 8.44 (d, 1H) 8.04 (d, 1H) 7.36 (dd, 1H).

Aufarbeitung

  1. customto give a colorless solution
  2. customkept at 20° C.
  3. stirringwell shaken
  4. extractionThe aqueous layer was back-extracted with ethyl acetate (1×100 mL)
  5. washwashed with water, brine
  6. dry with materialdried (MgSO4)
  7. customevaporated
  8. customThe crude material was purified by flash chromatography (silica gel, 60% to 80% ethyl acetate/hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-01bb357f79d64d5b8a0cefa7e9c80e6e
Quelldatensatz
uspto-grants-2014_02
Patentnummer
US08658646B2

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