Phosphorus oxybromide → 6-bromo-1-methyl-3-phenyl-4-(trifluoromethyl)-1H-pyrazolo[3,4-b]pyridine

HRID 402479

Reaktionsgleichung

Reaktionsgleichung von HRID 402479
[CH3:1][N:2]1[C:6]2[NH:7][C:8](=O)[CH:9]=[C:10]([C:11]([F:14])([F:13])[F:12])[C:5]=2[C:4]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[N:3]1.P(Br)(Br)([Br:24])=O>>[Br:24][C:8]1[N:7]=[C:6]2[N:2]([CH3:1])[N:3]=[C:4]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[C:5]2=[C:10]([C:11]([F:14])([F:13])[F:12])[CH:9]=1

Komponenten

3

Edukt 2

HCID 24613Phosphorus oxybromideHCID 1363765221-methyl-3-phenyl-4-(trifluoromethyl)-1H-pyrazolo[3,4-b]pyridin-6(7H)-one

Produkt 1

HCID 866720496-bromo-1-methyl-3-phenyl-4-(trifluoromethyl)-1H-pyrazolo[3,4-b]pyridineAusbeute 99,1 %

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

A mixture of 1-methyl-3-phenyl-4-(trifluoromethyl)-1H-pyrazolo[3,4-b]pyridin-6(7H)-one (1.0 g, 3.4 mmol) and POBr3 (0.962 g, 3.4 mmol) was heated at 120° C. for 3 h. The reaction mixture was cooled to it and poured into rapidly stirred ice cold water to obtain a solid product. The product was collected by filtration and dried under vacuum to yield an off-white solid (1.20 g, 99%). [1H-NMR (CDCl3, 300 MHz) δ 7.58 (s, 1H), 7.54-7.41 (m, 5H), 4.22 (s, 3H); LCMS RtA=1.943 min; [M+H]+=355.9]

Aufarbeitung

  1. temperatureThe reaction mixture was cooled to it
  2. additionpoured into rapidly stirred ice cold water
  3. customto obtain a solid product
  4. filtrationThe product was collected by filtration
  5. customdried under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-1153d49f2afd46318c3897977d979a51
Quelldatensatz
uspto-grants-2014_06
Patentnummer
US08742106B2

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