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Water → HCID 67492607, Verbindung

HRID 384074
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 384074
[C:1]([C:3]1([C:6]2[CH:7]=[C:8]([CH2:21][CH2:22][CH2:23][NH:24][C:25](=[O:31])[O:26][C:27]([CH3:30])([CH3:29])[CH3:28])[CH:9]=[C:10](B3OC(C)(C)C(C)(C)O3)[CH:11]=2)[CH2:5][CH2:4]1)#[N:2].I[C:33]1[CH:38]=[CH:37][N:36]=[C:35]2[N:39]([C:46]([C:59]3[CH:64]=[CH:63][CH:62]=[CH:61][CH:60]=3)([C:53]3[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=3)[C:47]3[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=3)[N:40]=[C:41]([C:42]([F:45])([F:44])[F:43])[C:34]=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>[C:1]([C:3]1([C:6]2[CH:7]=[C:8]([CH2:21][CH2:22][CH2:23][NH:24][C:25](=[O:31])[O:26][C:27]([CH3:29])([CH3:28])[CH3:30])[CH:9]=[C:10]([C:33]3[CH:38]=[CH:37][N:36]=[C:35]4[N:39]([C:46]([C:47]5[CH:48]=[CH:49][CH:50]=[CH:51][CH:52]=5)([C:53]5[CH:54]=[CH:55][CH:56]=[CH:57][CH:58]=5)[C:59]5[CH:60]=[CH:61][CH:62]=[CH:63][CH:64]=5)[N:40]=[C:41]([C:42]([F:44])([F:45])[F:43])[C:34]=34)[CH:11]=2)[CH2:4][CH2:5]1)#[N:2]
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 57969718HCID 57969718, Verbindung

Produkt 1

HCID 67492607HCID 67492607, VerbindungAusbeute 84,3 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418851HCID 178418851, VerbindungKatalysatorHCID 8857Ethyl AcetateLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

tert-Butyl N-[3-[3-(1-cyanocyclopropyl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]propyl]carbamate (50 mg, 0.1173 mmol) was dissolved in dioxane (2 mL) and 4-iodo-3-(trifluoromethyl)-1-trityl-pyrazolo[5,4-b]pyridine (65.14 mg, 0.1173 mmol) was added followed by sodium carbonate (176.0 μL of 2 M, 0.3519 mmol). The reaction mixture was degassed and filled with nitrogen 5 times then Pd[P(tBu)3]2 (8.994 mg, 0.01760 mmol) was added and the reaction heated at 60° C. overnight. After cooling, water was added and ethyl acetate. The aqueous layer was extracted three times with ethyl acetate, the combined organics were 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:Petrol ether to give tert-butyl 3-(3-(1-cyanocyclopropyl)-5-(3-(trifluoromethyl)-1-trityl-1H-pyrazolo[3,4-b]pyridin-4-yl)phenyl)propylcarbamate as a viscous oil (72 mg, 84%).

Aufarbeitung

  1. customThe reaction mixture 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 were 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-7f93b1bd6da242ac8b16ed01f1983588
Quelldatensatz
uspto-grants-2013_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08367697B2

Notizen zur Reaktion

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