Cesium fluoride → HCID 68668109, Verbindung

HRID 216364

Reaktionsgleichung

Reaktionsgleichung von HRID 216364
[CH3:1][N:2]1[C:6]([Sn](CCCC)(CCCC)CCCC)=[CH:5][CH:4]=[N:3]1.Br[C:21]1[CH:26]=[CH:25][C:24]([C:27]([OH:61])([CH2:31][C:32]2[N:33]([C:42]([C:55]3[CH:60]=[CH:59][CH:58]=[CH:57][CH:56]=3)([C:49]3[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=3)[C:43]3[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=3)[CH:34]=[C:35]([CH2:37][C:38]([CH3:41])([CH3:40])[CH3:39])[N:36]=2)[CH:28]([F:30])[F:29])=[CH:23][CH:22]=1.[F-].[Cs+]>O1CCCC1.[Pd](Cl)Cl.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH3:39][C:38]([CH3:41])([CH3:40])[CH2:37][C:35]1[N:36]=[C:32]([CH2:31][C:27]([C:24]2[CH:25]=[CH:26][C:21]([C:6]3[N:2]([CH3:1])[N:3]=[CH:4][CH:5]=3)=[CH:22][CH:23]=2)([OH:61])[CH:28]([F:29])[F:30])[N:33]([C:42]([C:49]2[CH:50]=[CH:51][CH:52]=[CH:53][CH:54]=2)([C:55]2[CH:60]=[CH:59][CH:58]=[CH:57][CH:56]=2)[C:43]2[CH:44]=[CH:45][CH:46]=[CH:47][CH:48]=2)[CH:34]=1

Komponenten

6

Edukt 3

HCID 25953Cesium fluorideHCID 218674551-Methyl-5-(tributylstannyl)-1H-pyrazoleHCID 68668368HCID 68668368, Verbindung

Produkt 1

HCID 68668109HCID 68668109, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6102075Dichlorobis(triphenylphosphine)palladiumKatalysatorHCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
75 °C

Versuchsvorschrift

Bis(triphenylphosphine) palladium (II) chloride (49 mg, 0.07 mmol) was added to a degassed, ambient temperature solution of 1-methyl-5-(tributylstannyl)-1H-pyrazole (259 mg, 0.70 mmol) and 2-(4-bromophenyl)-3-[4-(2,2-dimethylpropyl)-1-trityl-1H-imidazol-2-yl]-1,1-difluoropropan-2-ol (483 mg, 0.77 mmol) in tetrahydrofuran (15 mL). After stirring at 75° C. overnight, the reaction mixture was cooled and cesium fluoride (50% on celite) was added. After stirring vigorously at ambient temperature for 1 h, the reaction mixture was filtered, rinsing with ethyl acetate. The filtrate was washed with water, dried (magnesium sulfate), filtered and concentrated in vacuo. Chromatography over silica eluting with 0-100% ethyl acetate/hexane afforded 3-[4-(2,2-dimethylpropyl)-1-trityl-1H-imidazol-2-yl]-1,1-difluoro-2-[4-(1-methyl-1H-pyrazol-5-yl)phenyl]propan-2-ol.

Aufarbeitung

  1. temperaturethe reaction mixture was cooled
  2. stirringAfter stirring vigorously at ambient temperature for 1 h
  3. filtrationthe reaction mixture was filtered
  4. washrinsing with ethyl acetate
  5. washThe filtrate was washed with water
  6. dry with materialdried (magnesium sulfate)
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-67a203e52ab0405785e6459910bc177b
Quelldatensatz
uspto-grants-2012_06
Patentnummer
US08193228B2

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