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Cesium fluoride → HCID 25182570, Verbindung

HRID 500737
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 500737
C(OC([N:8]([C:16]1[C:21]([O:22][CH3:23])=[N:20][C:19](B2OC(C)(C)C(C)(C)O2)=[CH:18][N:17]=1)C(OC(C)(C)C)=O)=O)(C)(C)C.[F:33][CH:34]([F:53])[CH2:35][N:36]1[CH:40]=[C:39]([C:41]2[CH:46]=[CH:45][N:44]=[C:43]([NH:47][CH2:48][CH2:49][C:50]#[N:51])[N:42]=2)[C:38](I)=[N:37]1.[F-].[Cs+].[I-]>C(COC)OC>[NH2:8][C:16]1[N:17]=[CH:18][C:19]([C:38]2[C:39]([C:41]3[CH:46]=[CH:45][N:44]=[C:43]([NH:47][CH2:48][CH2:49][C:50]#[N:51])[N:42]=3)=[CH:40][N:36]([CH2:35][CH:34]([F:53])[F:33])[N:37]=2)=[N:20][C:21]=1[O:22][CH3:23]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 25953Cesium fluorideHCID 30165Iodide IonHCID 57856249HCID 57856249, VerbindungHCID 57856300HCID 57856300, Verbindung

Produkt 1

HCID 25182570HCID 25182570, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8071
1,2-Dimethoxyethane
Lösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

To a solution of the crude di-tert-butyl[3-methoxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrazin-2-yl]imidodicarbonate B-79-3 (0.6 mmol) in dimethoxyethane (2.5 mL) was added 3-{4-[1-(2,2-Difluoro-ethyl)-3-iodo-1H-pyrazol-4-yl]-pyrimidin-2-ylamino}-propionitrile B-33-3 (150 mg, 0.37 mmol) and Cesium Fluoride (1.1 mL of a 1M aqueous solution, 1.1 mmol). The resulting mixture was deoxygenated with a nitrogen bubbler for 5 min and then 1,1′-Bis(diphenylphosphino)ferrocene-palladium(II) dichloride dichloromethane complex (15 mg, 0.019 mmol) was added. The mixture was then heated in an 80° C. oil bath for 20 hours. LCMS indicated the iodide had been completely consumed. The mixture was partitioned between ethyl acetate and water. The aqueous layer was extracted with ethyl acetate. The combined organics were dried over magnesium sulfate and reduced to minimum volume. The residue was taken up in dimethoxyethane (3 mL) and then heated at 170° C. in the microwave for 25 minutes to thermolyze the tert-butoxycarbonyl groups. The resulting dark mixture was filtered through a 0.45μ filter and the filtrate reduced to minimum volume. The residue was purified by HPLC to give 59 mg (37%) of B-79 as a fluffy white solid after lyophilization of the desired fractions. 1H NMR (400 MHz, ACETONITRILE-d3) δ ppm 8.17 (s, 1H), 8.15 (d, J=5.05 Hz, 1H), 7.83 (s, 1H), 6.72 (d, J=5.31 Hz, 1H), 6.27 (tt, J=54.98, 3.76 Hz, 1H), 5.91 (br.t, J=5.18 Hz, 1H), 5.34 (br. s., 2H), 4.59 (td, J=14.65, 3.79 Hz, 2H), 3.76 (s, 3H), 3.55 (q, J=6.23 Hz, 2H), 2.64 (t, J=6.44 Hz, 2H)

Aufarbeitung

  1. customThe resulting mixture was deoxygenated with a nitrogen bubbler for 5 min
  2. addition1,1′-Bis(diphenylphosphino)ferrocene-palladium(II) dichloride dichloromethane complex (15 mg, 0.019 mmol) was added
  3. customhad been completely consumed
  4. customThe mixture was partitioned between ethyl acetate and water
  5. extractionThe aqueous layer was extracted with ethyl acetate
  6. dry with materialThe combined organics were dried over magnesium sulfate
  7. temperatureheated at 170° C. in the microwave for 25 minutes
  8. filtrationThe resulting dark mixture was filtered through
  9. filtrationa 0.45μ filter
  10. customThe residue was purified by HPLC
  11. customto give 59 mg (37%) of B-79 as a fluffy white solid after lyophilization of the desired fractions

Quellen und Nachweise

ORD-Eintrag
ord-68cc65dea29141e3bc635f467cf163df
Quelldatensatz
uspto-grants-2010_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07772246B2

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