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Potassium Carbonate → 2-[4-[(1E)-1-phenylmethoxyimino-2,3-dihydroinden-5-yl]-3-pyridin-4-ylpyrazol-1-yl]ethanol

HRID 1726397
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1726397
Br[C:2]1[C:3]([C:10]2[CH:15]=[CH:14][N:13]=[CH:12][CH:11]=2)=[N:4][N:5]([CH2:7][CH2:8][OH:9])[CH:6]=1.[CH2:16]([O:23]/[N:24]=[C:25]1\[CH2:26][CH2:27][C:28]2[C:33]\1=[CH:32][CH:31]=[C:30](B(O)O)[CH:29]=2)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C.O>[CH2:16]([O:23]/[N:24]=[C:25]1\[CH2:26][CH2:27][C:28]2[C:33]\1=[CH:32][CH:31]=[C:30]([C:2]1[C:3]([C:10]3[CH:15]=[CH:14][N:13]=[CH:12][CH:11]=3)=[N:4][N:5]([CH2:7][CH2:8][OH:9])[CH:6]=1)[CH:29]=2)[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 3

HCID 11430Potassium CarbonateHCID 672937372-(4-bromo-3-(pyridin-4-yl)-1H-pyrazol-1-yl)ethanolHCID 87623866[(1E)-1-phenylmethoxyimino-2,3-dihydroinden-5-yl]boronic acid2×

Produkt 1

HCID 876234382-[4-[(1E)-1-phenylmethoxyimino-2,3-dihydroinden-5-yl]-3-pyridin-4-ylpyrazol-1-yl]ethanolAusbeute 69,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962
Water
Lösungsmittel
HCID 6342AcetonitrileLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

To 2-(4-bromo-3-(pyridin-4-yl)-1H-pyrazol-1-yl)ethanol (100 mg; Example 4, step 3) in 7 mL acetonitrile and 3 mL water, was added 136 mg (E)-1-(benzyloxyimino)-2,3-dihydro-1H-inden-5-ylboronic acid (product of Example 2, Step 4), and 155 mg potassium carbonate. The mixture was purged with nitrogen and about 43 mg tetrakis(triphenyphosphine)palladium(0) catalyst was added. The mixture was heated at 80° C. After 1 hour, the reaction mixture was filtered through celite, the filter cake washed with ethyl acetate, and filtrate evaporated under vacuum. The residue was purified by chromatography, eluting with a mixture of 8:1 ethyl acetate-methanol to afford 110 mg (69% yield) product as a white solid. 1H NMR (CDCl3) was consistent with the desired structure. LC/MS showed one peak with a M+1 molecular ion of m/z 425.2 by positive ESI.

Aufarbeitung

  1. customThe mixture was purged with nitrogen and about 43 mg tetrakis(triphenyphosphine)palladium(0) catalyst
  2. additionwas added
  3. filtrationthe reaction mixture was filtered through celite
  4. washthe filter cake washed with ethyl acetate, and filtrate
  5. customevaporated under vacuum
  6. customThe residue was purified by chromatography
  7. washeluting with a mixture of 8:1 ethyl acetate-methanol

Quellen und Nachweise

ORD-Eintrag
ord-0e5a133cddc44114b3925d46895c6a00
Quelldatensatz
uspto-grants-2009_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07491829B2

Notizen zur Reaktion

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