Bromine → HCID 178490902, Verbindung

HRID 387522

Reaktionsgleichung

Reaktionsgleichung von HRID 387522
[CH3:1][O:2][C:3]1[CH:19]=[CH:18][C:6]([CH2:7][N:8]2[C:12]3[N:13]=[CH:14][CH:15]=[C:16]([OH:17])[C:11]=3[CH:10]=[N:9]2)=[CH:5][CH:4]=1.[Br:20]Br>C(O)C>[Br:20][C:15]1[CH:14]=[N:13][C:12]2[N:8]([CH2:7][C:6]3[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:19][CH:18]=3)[N:9]=[CH:10][C:11]=2[C:16]=1[OH:17]

Komponenten

4

Edukt 2

HCID 24408BromineHCID 178490904HCID 178490904, Verbindung

Produkt 1

HCID 178490902HCID 178490902, VerbindungAusbeute 83,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

A solution of 1-(4-methoxybenzyl)-1H-pyrazolo[3,4-b]pyridin-4-ol (10.00 g, 39.17 mmol, prepared as described in WO 2007/103308) in absolute ethanol (220 mL) was cooled to 0° C., treated dropwise with bromine (2.15 mL, 43.09 mmol) and stirred at 0° C. for 30 minutes. The ice bath was then removed, and the mixture was allowed to warm to room temperature. After 30 minutes, water (150 mL) and concentrated HCl (10 mL) were added to the slurry, and the mixture was stirred at room temperature for 10 minutes. The solid formed was filtered and washed with water (3×20 mL) followed by EtOH (2×20 mL). The solid collected was triturated with CH3CN, filtered, washed with additional CH3CN (2×10 mL), and air dried to provide 5-bromo-1-(4-methoxybenzyl)-1H-pyrazolo[3,4-b]pyridin-4-ol (10.90 g, 83% yield) as a solid. LCMS (APCI+) m/z 333.9 (M+H)+, Retention time=2.33 minutes.

Aufarbeitung

  1. customThe ice bath was then removed
  2. temperatureto warm to room temperature
  3. waitAfter 30 minutes
  4. additionwater (150 mL) and concentrated HCl (10 mL) were added to the slurry
  5. stirringthe mixture was stirred at room temperature for 10 minutes
  6. customThe solid formed
  7. filtrationwas filtered
  8. washwashed with water (3×20 mL)
  9. customThe solid collected
  10. customwas triturated with CH3CN
  11. filtrationfiltered
  12. washwashed with additional CH3CN (2×10 mL), and air
  13. customdried

Quellen und Nachweise

ORD-Eintrag
ord-a6eab61b674b40a793899ffa80db9804
Quelldatensatz
uspto-grants-2013_02
Patentnummer
US08372842B2

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