Piperidine → 6-ethynyl-N-phenylimidazo[1,2-a]pyridine-2-carboxamide

HRID 1878467Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1878467
[C:1]1([NH:7][C:8]([C:10]2[N:11]=[C:12]3[CH:17]=[CH:16][C:15]([C:18]#N)=[CH:14][N:13]3[CH:20]=2)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:21][Si](C#C)(C)C.N1CCCCC1>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.[Cl-].[NH4+]>[C:18]([C:15]1[CH:16]=[CH:17][C:12]2[N:13]([CH:20]=[C:10]([C:8]([NH:7][C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)=[O:9])[N:11]=2)[CH:14]=1)#[CH:21]

Komponenten

6

Edukt 3

HCID 8082PiperidineHCID 66111TrimethylsilylacetyleneHCID 44135940N-phenyl-6-cyanoimidazo[1,2-a]pyridine-2-carboxamide2×

Produkt 1

HCID 247716676-ethynyl-N-phenylimidazo[1,2-a]pyridine-2-carboxamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418476HCID 178418476, VerbindungKatalysatorHCID 25517Ammonium ChlorideLösungsmittel

Reaktionsbedingungen

Temperatur
25 °C

Versuchsvorschrift

0.2 g of 6-iodo-N-phenylimidazo[1,2-a]pyridine-2-carboxamide (Intermediate 2), 156 μL of trimethylsilylacetylene, 20 mg of dichlorobis(triphenylphosphine)palladium and 2 mL of piperidine are placed in a 20 mL microwave tube. The mixture is heated for 15 minutes in a microwave machine set at 130° C. After cooling, the mixture is poured into 50 mL of saturated aqueous ammonium chloride solution. The resulting mixture is extracted twice with 70 mL of ethyl ether. The combined organic phases are separated out by settling, dried and concentrated to dryness under reduced pressure. The residue is taken up in 4 mL of a 1M solution of tetrabutylammonium fluoride in THF and stirred for 16 hours at 25° C. After evaporating the reaction medium to dryness, the residue is chromatographed on silica, eluting with a mixture of cyclohexane and ethyl acetate (gradient from 0 to 35%) to give 30 mg of 6-ethynyl-N-phenylimidazo[1,2-a]pyridine-2-carboxamide in the form of a beige-coloured solid.

Aufarbeitung

  1. temperatureThe mixture is heated for 15 minutes in a microwave machine
  2. customset at 130° C
  3. temperatureAfter cooling
  4. extractionThe resulting mixture is extracted twice with 70 mL of ethyl ether
  5. customThe combined organic phases are separated out
  6. customdried
  7. concentrationconcentrated to dryness under reduced pressure
  8. customAfter evaporating the reaction medium to dryness
  9. customthe residue is chromatographed on silica
  10. washeluting with a mixture of cyclohexane and ethyl acetate (gradient from 0 to 35%)

Quellen und Nachweise

ORD-Eintrag
ord-94ad79d68c754e378591129efab5223a
Quelldatensatz
uspto-grants-2012_11
Patentnummer
US08314109B2

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