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Cesium carbonate → tert-butyl3-{[4-chloro-3-(3-chloro-5-cyanophenoxy)-5-fluorophenoxy]methyl}-6-fluoro-1H-pyrazolo[3,4-b]pyridine-1-carboxylate

HRID 1157421
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1157421
[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([O:10][C:11]2[CH:16]=[C:15]([OH:17])[CH:14]=[C:13]([F:18])[C:12]=2[Cl:19])[CH:9]=1)[C:5]#[N:6].C([O-])([O-])=O.[Cs+].[Cs+].Br[CH2:27][C:28]1[C:36]2[C:31](=[N:32][C:33]([F:37])=[CH:34][CH:35]=2)[N:30]([C:38]([O:40][C:41]([CH3:44])([CH3:43])[CH3:42])=[O:39])[N:29]=1>CN1C(=O)CCC1.CCOC(C)=O>[C:41]([O:40][C:38]([N:30]1[C:31]2=[N:32][C:33]([F:37])=[CH:34][CH:35]=[C:36]2[C:28]([CH2:27][O:17][C:15]2[CH:14]=[C:13]([F:18])[C:12]([Cl:19])=[C:11]([O:10][C:8]3[CH:7]=[C:4]([C:5]#[N:6])[CH:3]=[C:2]([Cl:1])[CH:9]=3)[CH:16]=2)=[N:29]1)=[O:39])([CH3:44])([CH3:43])[CH3:42]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 3

HCID 10796Cesium carbonateHCID 25132591tert-butyl 3-(bromomethyl)-6-fluoro-1H-pyrazolo[3,4-b]pyridine-1-carboxylateHCID 445509693-Chloro-5-(2-chloro-3-fluoro-5-hydroxyphenoxy)benzonitrile

Produkt 1

HCID 44549123tert-butyl3-{[4-chloro-3-(3-chloro-5-cyanophenoxy)-5-fluorophenoxy]methyl}-6-fluoro-1H-pyrazolo[3,4-b]pyridine-1-carboxylateAusbeute 85 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8857Ethyl AcetateLösungsmittelHCID 13387N-methyl-2-pyrrolidoneLösungsmittel

Versuchsvorschrift

Under a nitrogen atmosphere, 3-chloro-5-(2-chloro-3-fluoro-5-hydroxyphenoxy)benzonitrile (50-5) (150 mg, 0.503 mmol) was dissolved in NMP (4 mL, 0.1 M). Next, Cs2CO3 (164 mg, 0.503 mmol) was added and the reaction was allowed to stir at room temperature for 15 minutes. Then, tert-butyl-3-(bromomethyl)-6-fluoro-1H-pyrazolo[3,4-b]pyridine-1-carboxylate (37-5) (166 mg, 0.503 mmol, prepared using the procedure set forth in Example 37) was added to the reaction. The reaction was stirred at room temperature for 2 hours. It was then diluted with EtOAc (4 mL). It was partitioned with water (3 mL) and then extracted with EtOAc (3×4 mL). The organic extracts were then washed with water (3×4 mL) and brine (1×4 mL), dried over sodium sulfate and concentrated. Silica gel chromatography (1%-20% EtOAc/Hexanes) gave tert-butyl3-{[4-chloro-3-(3-chloro-5-cyanophenoxy)-5-fluorophenoxy]-methyl}-6-fluoro-1H-pyrazolo[3,4-b]pyridine-1-carboxylate (50-6) (230 mg, 85%). LCMS (ES) m/z 446.9 (M-BOC)+.

Aufarbeitung

  1. additionwas added to the reaction
  2. stirringThe reaction was stirred at room temperature for 2 hours
  3. customIt was partitioned with water (3 mL)
  4. extractionextracted with EtOAc (3×4 mL)
  5. washThe organic extracts were then washed with water (3×4 mL) and brine (1×4 mL)
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-09613ba03eaa4f29a1b6e16cc7121008
Quelldatensatz
uspto-grants-2010_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07807684B2

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