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

HRID 570544Notes

Reaction equation

HRID 570544 reaction equation
[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

Participants

6

Reactant 4

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

Product 1

HCID 866921116-Chloro-1-(2-fluorobenzyl)-1H-indazole-3-carbonitrileYield 102.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-eddddf4136b64a6884bceb8be2a2c429
Source dataset
uspto-grants-2015_05
Patent number
US09023849B2

Reaction notes

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