Imidazole → HCID 24826450, compound

HRID 230702Notes

Reaction equation

HRID 230702 reaction equation
[H-].[Na+].[NH:3]1[CH:7]=[CH:6][N:5]=[CH:4]1.Cl[CH2:9][C:10]1[CH:15]=[CH:14][C:13]([N:16]2[C:24]3[CH2:23][CH2:22][CH2:21][CH2:20][C:19]=3[C:18]([C:25]([F:28])([F:27])[F:26])=[N:17]2)=[CH:12][CH:11]=1>CN(C=O)C>[N:3]1([CH2:9][C:10]2[CH:15]=[CH:14][C:13]([N:16]3[C:24]4[CH2:23][CH2:22][CH2:21][CH2:20][C:19]=4[C:18]([C:25]([F:28])([F:26])[F:27])=[N:17]3)=[CH:12][CH:11]=2)[CH:7]=[CH:6][N:5]=[CH:4]1

Participants

5

Reactant 3

HCID 795ImidazoleHCID 24758Sodium hydrideHCID 509927231-[4-(chloromethyl)phenyl]-3-(trifluoromethyl)-4,5,6,7-tetrahydro-1H-indazole

Product 1

HCID 24826450HCID 24826450, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

Sodium hydride (60% in mineral oil, 14.0 mg; 0.35 mmol) was added in one portion to a room temperature stirring solution of imidazole (11.5 mg; 0.17 mmol) in anhydrous DMF (1 mL). After stirring at this temperature for 1 hour, a solution of 1-[4-(chloromethyl)phenyl]-3-(trifluoromethyl)-4,5,6,7-tetrahydro-1H-indazole (61.2 mg; 0.19 mmol) in anhydrous DMF (0.4 mL) was added in one portion and the resulting mixture stirred at room temperature for a further 16 hours. The reaction was quenched with aqueous hydrochloric acid (0.2 M; 0.2 mL), and purified by SCX column chromatography, giving the title compound as a yellow oil (51.8 mg; 89%).

Workup

  1. stirringthe resulting mixture stirred at room temperature for a further 16 hours
  2. customThe reaction was quenched with aqueous hydrochloric acid (0.2 M; 0.2 mL)
  3. custompurified by SCX column chromatography

Sources & evidence

ORD record
ord-6461b962ed4b470eaf37a5505a814266
Source dataset
uspto-grants-2009_07
Patent number
US07566735B2

Reaction notes

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