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Water → HCID 67492851, Verbindung

HRID 384080
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 384080
CC1(C)C(C)(C)OB([C:9]2[CH:10]=[C:11]([C:15]3([CH2:19][NH:20][C:21](=[O:27])[O:22][C:23]([CH3:26])([CH3:25])[CH3:24])[CH2:18][O:17][CH2:16]3)[CH:12]=[CH:13][CH:14]=2)O1.I[C:30]1[CH:35]=[CH:34][N:33]=[C:32]2[N:36]([C:43]([C:56]3[CH:61]=[CH:60][CH:59]=[CH:58][CH:57]=3)([C:50]3[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=3)[C:44]3[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=3)[N:37]=[C:38]([C:39]([F:42])([F:41])[F:40])[C:31]=12.C(=O)([O-])[O-].[Na+].[Na+].O>O1CCOCC1.CC(C)([P](C(C)(C)C)([Pd][P](C(C)(C)C)(C(C)(C)C)C(C)(C)C)C(C)(C)C)C.C(OCC)(=O)C>[F:40][C:39]([F:42])([F:41])[C:38]1[C:31]2[C:32](=[N:33][CH:34]=[CH:35][C:30]=2[C:9]2[CH:10]=[C:11]([C:15]3([CH2:19][NH:20][C:21](=[O:27])[O:22][C:23]([CH3:25])([CH3:24])[CH3:26])[CH2:16][O:17][CH2:18]3)[CH:12]=[CH:13][CH:14]=2)[N:36]([C:43]([C:56]2[CH:61]=[CH:60][CH:59]=[CH:58][CH:57]=2)([C:50]2[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=2)[C:44]2[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=2)[N:37]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

8

Edukt 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 579697084-Iodo-3-(trifluoromethyl)-1-(triphenylmethyl)-1H-pyrazolo[3,4-b]pyridineHCID 57969842HCID 57969842, Verbindung

Produkt 1

HCID 67492851HCID 67492851, VerbindungAusbeute 50,3 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418851HCID 178418851, VerbindungKatalysator
HCID 8857Ethyl AcetateLösungsmittel
HCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

tert-Butyl N-[[3-[3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]oxetan-3-yl]methyl]carbamate (65 mg, 0.1670 mmol) was dissolved in dioxane (3 mL) and 4-iodo-3-(trifluoromethyl)-1-trityl-pyrazolo[3,4-b]pyridine (92.74 mg, 0.1670 mmol) was added followed by sodium carbonate (250.5 μL of 2 M, 0.5010 mmol). The reaction was degassed and filled with nitrogen 5 times then Pd[P(tBu)3]2 (12.80 mg, 0.02505 mmol) was added. The reaction was heated at 60° C. overnight. After cooling, water was added followed by ethyl acetate. The aqueous layer was extracted three times with ethyl acetate, the combined organics washed with brine, dried over MgSO4, filtered and the solvent removed under reduced pressure. The crude product was purified on silica (Companion, 12 g) eluting with 2.5-50% EtOAc:Pet.ether to give tert-butyl N-[[3-[3-[3-(trifluoromethyl)-1-trityl-pyrazolo[3,4-b]pyridin-4-yl]phenyl]oxetan-3-yl]methyl]carbamate as a white foam (58 mg, 50%).

Aufarbeitung

  1. customThe reaction was degassed
  2. additionfilled with nitrogen 5 times
  3. temperatureAfter cooling
  4. extractionThe aqueous layer was extracted three times with ethyl acetate
  5. washthe combined organics washed with brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. customthe solvent removed under reduced pressure
  9. customThe crude product was purified on silica (Companion, 12 g)
  10. washeluting with 2.5-50% EtOAc

Quellen und Nachweise

ORD-Eintrag
ord-2bca417729a540b1ada950ff920ce014
Quelldatensatz
uspto-grants-2013_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08367697B2

Notizen zur Reaktion

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