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Cesium carbonate → 7-tert-butyl 1-methyl 3-phenyl-5,6-dihydroimidazo[1,5-a]pyrazine-1,7(8H)-dicarboxylate

HRID 2110192
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2110192
Br[C:2]1[N:6]2[CH2:7][CH2:8][N:9]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:10][C:5]2=[C:4]([C:18]([O:20][CH3:21])=[O:19])[N:3]=1.[C:22]1(B(O)O)[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.C(=O)([O-])[O-].[Cs+].[Cs+].C([O-])(O)=O.[Na+]>C1(C)C=CC=CC=1>[C:22]1([C:2]2[N:6]3[CH2:7][CH2:8][N:9]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:10][C:5]3=[C:4]([C:18]([O:20][CH3:21])=[O:19])[N:3]=2)[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 10796Cesium carbonateHCID 66827Phenylboronic AcidHCID 516892Sodium BicarbonateHCID 576351407-(tert-Butyl) 1-methyl 3-bromo-5,6-dihydroimidazo[1,5-a]pyrazine-1,7(8H)-dicarboxylate

Produkt 1

HCID 576350867-tert-butyl 1-methyl 3-phenyl-5,6-dihydroimidazo[1,5-a]pyrazine-1,7(8H)-dicarboxylateAusbeute 70 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
110 °C

Versuchsvorschrift

To around-bottomed flask charged with Intermediate 1H (2 g, 5.55 mmol), phenyl boronic acid (2.07 g, 16.65 mmol), [Pd-(dppf)Cl2] (0.45 g, 10 mol %), and cesium carbonate (5.45 g, 16.65 mmol) was added toluene (anhydrous and de-gassed; 80 mL). The reaction mixture was heated to 110° C. while stirring under argon for 6 hours. After cooling to room temperature, saturated aqueous NaHCO3 solution was added and the mixture was extracted three times with ethyl acetate. The combined extracts were dried over anhydrous MgSO4, filtered and concentrated under reduced pressure to give the crude product. Purification by column chromatography (silica), eluting with ethyl acetate/hexane mixtures, provided Intermediate 3A as a white solid (70% yield). 1H-NMR (400 MHz, CDCl3) δ: 1.52 (s, 9H), 3.79 (m, 2H), 3.93 (s, 3H), 4.12 (m, 2H), 5.00 (s, 2H), 7.43-7.47 (m, 3H), 7.63-7.66 (m, 2H). LCMS (+ESI) m/z 358.28 [M+H]+.

Aufarbeitung

  1. temperatureAfter cooling to room temperature
  2. extractionthe mixture was extracted three times with ethyl acetate
  3. dry with materialThe combined extracts were dried over anhydrous MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customto give the crude product
  7. customPurification by column chromatography (silica)
  8. washeluting with ethyl acetate/hexane mixtures

Quellen und Nachweise

ORD-Eintrag
ord-385deadc93e24cb5939113a4996e16cd
Quelldatensatz
uspto-grants-2009_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07517874B2

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