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

HRID 505551Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 505551
[Cl:1][C:2]1[C:9]([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:8][C:7]([Cl:21])=[CH:6][C:3]=1[C:4]#[N:5].C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH2:29][C:30]1[C:38]2[C:33](=[N:34][CH:35]=[CH:36][CH:37]=2)[N:32]([C:39]([O:41][C:42]([CH3:45])([CH3:44])[CH3:43])=[O:40])[N:31]=1>CN(C=O)C>[Cl:20][C:12]1[CH:13]=[CH:14][C:15]2[N:16]([CH2:29][C:30]3[C:38]4[C:33](=[N:34][CH:35]=[CH:36][CH:37]=4)[N:32]([C:39]([O:41][C:42]([CH3:45])([CH3:44])[CH3:43])=[O:40])[N:31]=3)[N:17]=[N:18][C:19]=2[C:11]=1[O:10][C:9]1[CH:8]=[C:7]([Cl:21])[CH:6]=[C:3]([C:4]#[N:5])[C:2]=1[Cl:1]

Komponenten

5

Edukt 3

HCID 10796Cesium carbonateHCID 10828872tert-Butyl 3-(bromomethyl)-1H-pyrazolo[3,4-b]pyridine-1-carboxylateHCID 178509931HCID 178509931, Verbindung

Produkt 1

HCID 68428123tert-butyl 3-{[5-chloro-4-(2,5-dichloro-3-cyanophenoxy)-1H-1,2,3-benzotriazol-1-yl]methyl}-1H-pyrazolo[3,4-b]pyridine-1-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel2×

Versuchsvorschrift

2,5-dichloro-3-[(5-chloro-1H-1,2,3-benzotriazol-4-yl)oxy]benzonitrile (1.00 g, 2.94 mmol) and cesium carbonate (1.15 g, 3.53 mmol) were suspended in dry DMF (10 mL) under N2 and tert-butyl 3-(bromomethyl)-1H-pyrazolo[3,4-b]pyridine-1-carboxylate (0.965 g, 3.09 mmol) was added as a solution in DMF (5 mL) at room temperature. After 1 hour, the reaction mixture was quenched with saturated aqueous ammonium chloride (20 mL) and diluted with water (50 mL). The mixture was then extracted with ethyl acetate (2×100 mL). The combined organic fractions were washed with water (3×100 mL), dried (MgSO4), filtered and the solvent was evaporated under reduced pressure. The resulting residue was purified by automated column chromatography on silica gel (120 g) eluting with 25-50% EtOAc/hexanes. LRMS (M+1)=569.6.

Aufarbeitung

  1. customthe reaction mixture was quenched with saturated aqueous ammonium chloride (20 mL)
  2. additiondiluted with water (50 mL)
  3. extractionThe mixture was then extracted with ethyl acetate (2×100 mL)
  4. washThe combined organic fractions were washed with water (3×100 mL)
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. customthe solvent was evaporated under reduced pressure
  8. customThe resulting residue was purified by automated column chromatography on silica gel (120 g)
  9. washeluting with 25-50% EtOAc/hexanes

Quellen und Nachweise

ORD-Eintrag
ord-eb789e4a68ad485a996cc019bd6397b5
Quelldatensatz
uspto-grants-2010_08
Patentnummer
US07781454B2

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