Benzoyl Peroxide → tert-Butyl 3-(bromomethyl)-1H-pyrazolo[3,4-b]pyridine-1-carboxylate

HRID 343120Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 343120
[CH3:1][C:2]1[C:10]2[C:5](=[N:6][CH:7]=[CH:8][CH:9]=2)[N:4]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[N:3]=1.[Br:18]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[Br:18][CH2:1][C:2]1[C:10]2[C:5](=[N:6][CH:7]=[CH:8][CH:9]=2)[N:4]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[N:3]=1

Komponenten

5

Edukt 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 57370583Tert-butyl 3-methyl-1H-pyrazolo[3,4-B]pyridine-1-carboxylate

Produkt 1

HCID 10828872tert-Butyl 3-(bromomethyl)-1H-pyrazolo[3,4-b]pyridine-1-carboxylateAusbeute 52,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 5943Carbon TetrachlorideLösungsmittel

Versuchsvorschrift

A stirring solution of 240 mg (1.03 mmol) of 3-Methyl-1 tert-butoxycarbonyl-pyrazolo[3,4-b]pyridine, prepared as in Part B, in 10 mL of CCl4 is heated to reflux, and then a mixture of 220 mg (1.23 mmol, 1.2 equiv) of N-bromosuccinimide and 25 mg (0.10 mmol, 0.1 equiv) of benzoyl peroxide is added all at once as a solid. The resulting solution is heated at reflux for 3.5 h, then cooled to RT. The reaction mixture is filtered through a pad of Celite to remove the precipitated succinimide, and the solvent is removed in vacuo. Purification of the crude material by silica gel flash column chromatography using hexane/EtOAc 3/1 as eluent afforded 170 mg of the title compound as a white solid: 1H NMR (CDCl3, 400 MHz) δ8.75 (dd, 1H, J=1.4, 4.6), 8.21 (dd, 1H, J=1.4, 8.0), 7.32 (dd, 1H, J=4.6, 8.0), 4.74 (s, 2H), 1.70 (s, 9H).

Aufarbeitung

  1. temperatureto reflux
  2. additionis added all at once as a solid
  3. temperatureThe resulting solution is heated
  4. temperatureat reflux for 3.5 h
  5. filtrationThe reaction mixture is filtered through a pad of Celite
  6. customto remove the precipitated succinimide
  7. customthe solvent is removed in vacuo
  8. customPurification of the crude material by silica gel flash column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-e9db1058ccff47018fcce5de052021c6
Quelldatensatz
uspto-grants-1999_01
Patentnummer
US05859007

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