Water → 6-Chloro-1-(2-fluorobenzyl)-1H-indazole-3-carbonitrile

HRID 570544Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 570544
[F:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH2:4]Br.[Cl:10][C:11]1[CH:19]=[C:18]2[C:14]([C:15]([C:20]#[N:21])=[N:16][NH:17]2)=[CH:13][CH:12]=1.C(=O)([O-])[O-].[K+].[K+].O>CN(C=O)C>[Cl:10][C:11]1[CH:19]=[C:18]2[C:14]([C:15]([C:20]#[N:21])=[N:16][N:17]2[CH2:4][C:3]2[CH:6]=[CH:7][CH:8]=[CH:9][C:2]=2[F:1])=[CH:13][CH:12]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 67968alpha-Bromo-o-fluorotolueneHCID 534084026-Chloro-1H-indazole-3-carbonitrile

Produkt 1

HCID 866921116-Chloro-1-(2-fluorobenzyl)-1H-indazole-3-carbonitrileAusbeute 102,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel2×

Versuchsvorschrift

Under argon, 2.45 ml (14.2 mmol) of 2-fluorobenzyl bromide, dissolved in 10 ml DMF, were added to a mixture of 2.3 g (12.9 mmol) of 6-chloro-1H-indazole-3-carbonitrile (WO 2011/149921, Expl. 58C) and 2.15 g (15.5 mmol) of potassium carbonate in 40 ml of DMF, and the mixture was stirred at RT overnight. Then the mixture was poured onto 90 ml of water and the mixture was stirred at room temperature for 30 min. The precipitated solids were filtered off, washed with water and dried under high vacuum overnight. 3.77 g of the title compound were obtained as a crude product.

Aufarbeitung

  1. stirringthe mixture was stirred at room temperature for 30 min
  2. filtrationThe precipitated solids were filtered off
  3. washwashed with water
  4. customdried under high vacuum overnight

Quellen und Nachweise

ORD-Eintrag
ord-eddddf4136b64a6884bceb8be2a2c429
Quelldatensatz
uspto-grants-2015_05
Patentnummer
US09023849B2

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