Cesium carbonate → HCID 72203564, Verbindung

HRID 629097Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 629097
Br[C:2]1[C:3]([C:22]([F:25])([F:24])[F:23])=[N:4][CH:5]=[C:6]([CH:21]=1)[C:7]([NH:9][C:10]1[CH:15]=[CH:14][C:13]([O:16][C:17]([F:20])([F:19])[F:18])=[CH:12][CH:11]=1)=[O:8].[N:26]1[CH:31]=[C:30](B(O)O)[CH:29]=[N:28][CH:27]=1.C([O-])([O-])=O.[Cs+].[Cs+]>O.O1CCOCC1>[N:26]1[CH:31]=[C:30]([C:2]2[C:3]([C:22]([F:25])([F:24])[F:23])=[N:4][CH:5]=[C:6]([CH:21]=2)[C:7]([NH:9][C:10]2[CH:15]=[CH:14][C:13]([O:16][C:17]([F:20])([F:19])[F:18])=[CH:12][CH:11]=2)=[O:8])[CH:29]=[N:28][CH:27]=1

Komponenten

6

Edukt 3

HCID 10796Cesium carbonateHCID 2795193(Pyrimidin-5-yl)boronic acidHCID 89907016HCID 89907016, Verbindung

Produkt 1

HCID 72203564HCID 72203564, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittel2×HCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

5-Bromo-N-(4-(trifluoromethoxy)phenyl)-6-(trifluoromethyl)nicotinamide (Stage 57.1, 125.7 mg, 0.293 mmol), pyrimidin-5-ylboronic acid (43.6 mg, 0.352 mmol), Cs2CO3 (191 mg, 0.586 mmol), PdCl2(dppf)-(CH2Cl2) (23.92 mg, 0.029 mmol), water (2 mL) and dioxane (8 mL) were added to a vial, which was sealed, evacuated/purged with argon and the RM was stirred at 70° C. for 2.5 h. The solvent was evaporated off under reduced pressure to give a residue which was treated with water and extracted with EtOAc. The combined extracts were washed with water and brine, dried over Na2SO4 and the solvent was evaporated off under reduced pressure to give the crude product which was purified by flash chromatography (Silica gel column, 25 g, n-hexane/EtOAc) and recrystallized from n-hexane/EtOAc to give the title compound as a pink powder. UPLC-MS (Condition 2) tR=1.07 min, m/z=429 [M+H]+.

Aufarbeitung

  1. customwas sealed
  2. customevacuated/purged with argon
  3. customThe solvent was evaporated off under reduced pressure
  4. customto give a residue which
  5. extractionextracted with EtOAc
  6. washThe combined extracts were washed with water and brine
  7. dry with materialdried over Na2SO4
  8. customthe solvent was evaporated off under reduced pressure
  9. customto give the crude product which
  10. customwas purified by flash chromatography (Silica gel column, 25 g, n-hexane/EtOAc)
  11. customrecrystallized from n-hexane/EtOAc

Quellen und Nachweise

ORD-Eintrag
ord-32c65b7f729545b59967f6def667683c
Quelldatensatz
uspto-grants-2016_04
Patentnummer
US09315489B2

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