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Acetonitrile → 3-(1-ethyl-1H-imidazo[4,5-c]pyridin-2-yl)-5-phenylpyrazin-2-amine

HRID 2373168
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Reaktionsgleichung

Reaktionsgleichung von HRID 2373168
Br[C:2]1[N:3]=[C:4]([C:9]2[N:10]([CH2:18][CH3:19])[C:11]3[CH:16]=[CH:15][N:14]=[CH:13][C:12]=3[N:17]=2)[C:5]([NH2:8])=[N:6][CH:7]=1.[C:20]1(B(O)O)[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.C(=O)([O-])[O-].[K+].[K+].C(#N)C>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.O>[CH2:18]([N:10]1[C:11]2[CH:16]=[CH:15][N:14]=[CH:13][C:12]=2[N:17]=[C:9]1[C:4]1[C:5]([NH2:8])=[N:6][CH:7]=[C:2]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[N:3]=1)[CH3:19]
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Komponenten

7

Edukt 4

HCID 6342AcetonitrileHCID 11430Potassium CarbonateHCID 66827Phenylboronic AcidHCID 598524085-bromo-3-(1-ethyl-1H-imidazo[4,5-c]pyridin-2-yl)pyrazin-2-amine

Produkt 1

HCID 598524123-(1-ethyl-1H-imidazo[4,5-c]pyridin-2-yl)-5-phenylpyrazin-2-amineAusbeute 23,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418476HCID 178418476, VerbindungKatalysator
HCID 962WaterLösungsmittel

Versuchsvorschrift

5-Bromo-3-(1-ethyl-1H-imidazo[4,5-c]pyridin-2-yl)pyrazin-2-amine (0.038 g, 0.12 mmol) (see Example 2), phenyl boronic acid (0.034 g, 0.27 mmol), dichlorobis(triphenylphosphine)palladium(II) (0.009 g, 0.012 mmol), potassium carbonate (0.045 g, 0.32 mmol), and an 8:1 mixture of acetonitrile:water (3 mL) were combined and subjected to 150° C. for 5 minutes in a SmithSynthesizer microwave. The resulting heterogeneous, black mixture was filtered through a celite pad, which was then washed with ethyl acetate and water. The mixture is extracted into ethyl acetate (×3) and washed with water and saturated sodium chloride. The combined organic layers are dried over magnesium sulfate, filtered and concentrated. The residue is purified on silica, eluting with 2.5% methanol in chloroform to afford the title compound (0.009 g, 23%).

Aufarbeitung

  1. filtrationThe resulting heterogeneous, black mixture was filtered through a celite pad, which
  2. washwas then washed with ethyl acetate and water
  3. extractionThe mixture is extracted into ethyl acetate (×3)
  4. washwashed with water and saturated sodium chloride
  5. dry with materialThe combined organic layers are dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue is purified on silica
  9. washeluting with 2.5% methanol in chloroform

Quellen und Nachweise

ORD-Eintrag
ord-e4d211eb2d4f4e7e94e8b36b9ac1bd4a
Quelldatensatz
uspto-grants-2008_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07459454B2

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