Cesium carbonate → tert-Butyl 3-{[5-chloro-4-(3-chloro-5-cyanophenoxy)-1H-1,2,3-benzotriazol-1-yl]methyl}-1H-pyrazolo[3,4-b]pyridine-1-carboxylate

HRID 505517

Reaktionsgleichung

Reaktionsgleichung von HRID 505517
[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([O:10][C:11]2[C:19]3[N:18]=[N:17][NH:16][C:15]=3[CH:14]=[CH:13][C:12]=2[Cl:20])[CH:9]=1)[C:5]#[N:6].C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH2:28][C:29]1[C:37]2[C:32](=[N:33][CH:34]=[CH:35][CH:36]=2)[N:31]([C:38]([O:40][C:41]([CH3:44])([CH3:43])[CH3:42])=[O:39])[N:30]=1>CN(C=O)C>[Cl:20][C:12]1[CH:13]=[CH:14][C:15]2[N:16]([CH2:28][C:29]3[C:37]4[C:32](=[N:33][CH:34]=[CH:35][CH:36]=4)[N:31]([C:38]([O:40][C:41]([CH3:44])([CH3:43])[CH3:42])=[O:39])[N:30]=3)[N:17]=[N:18][C:19]=2[C:11]=1[O:10][C:8]1[CH:7]=[C:4]([C:5]#[N:6])[CH:3]=[C:2]([Cl:1])[CH:9]=1

Komponenten

5

Edukt 3

HCID 10796Cesium carbonateHCID 10828872tert-Butyl 3-(bromomethyl)-1H-pyrazolo[3,4-b]pyridine-1-carboxylate2×HCID 178509930HCID 178509930, Verbindung

Produkt 1

HCID 56833850tert-Butyl 3-{[5-chloro-4-(3-chloro-5-cyanophenoxy)-1H-1,2,3-benzotriazol-1-yl]methyl}-1H-pyrazolo[3,4-b]pyridine-1-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel2×

Versuchsvorschrift

To 3-chloro-5-[(5-chloro-1H-1,2,3-benzotriazol-4-yl)oxy]benzonitrile (0.006 g, 0.020 mmol) and cesium carbonate (0.0077 g, 0.024 mmol) suspended in DMF (1 mL) at room temperature was added tert-butyl 3-(bromomethyl)-1H-pyrazolo[3,4-b]pyridine-1-carboxylate (=Intermediate 1; 0.0068 g, 0.022 mmol) as a solution in DMF (0.5 mL). After stirring for 1 hour at room temperature, the reaction mixture was quenched with aqueous ammonium chloride (2 mL), and the quenched mixture was extracted with ethyl acetate (2×10 mL). The combined organic fractions were washed with water (3×10 mL), dried over MgSO4, filtered and concentrated under reduced pressure. The resulting residue was subjected to automated silica gel chromatography eluting with a gradient of 25-50% ethyl acetate in hexanes to afford the title product. LRMS (M+1)=435.7

Aufarbeitung

  1. customthe reaction mixture was quenched with aqueous ammonium chloride (2 mL)
  2. extractionthe quenched mixture was extracted with ethyl acetate (2×10 mL)
  3. washThe combined organic fractions were washed with water (3×10 mL)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. washeluting with a gradient of 25-50% ethyl acetate in hexanes

Quellen und Nachweise

ORD-Eintrag
ord-81e0a685eed14ba689ac16ef2a6a500a
Quelldatensatz
uspto-grants-2010_08
Patentnummer
US07781454B2

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