Sodium hydride → HCID 86603022, compound

HRID 735457Notes

Reaction equation

HRID 735457 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([C:10]3[N:11]([CH2:23][C:24]4[C:29]([F:30])=[CH:28][C:27]([F:31])=[CH:26][C:25]=4[F:32])[N:12]=[C:13]4[C:18]=3[CH:17]=[CH:16][CH:15]=[C:14]4[C:19]([F:22])([F:21])[F:20])=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.[H-].[Na+].[Cl:35][C:36]1[CH:43]=[C:42]([Cl:44])[CH:41]=[CH:40][C:37]=1[CH2:38]Br>CN(C=O)C>[Cl:35][C:36]1[CH:43]=[C:42]([Cl:44])[CH:41]=[CH:40][C:37]=1[CH2:38][N:1]1[C:9]2[C:4](=[CH:5][C:6]([C:10]3[N:11]([CH2:23][C:24]4[C:25]([F:32])=[CH:26][C:27]([F:31])=[CH:28][C:29]=4[F:30])[N:12]=[C:13]4[C:18]=3[CH:17]=[CH:16][CH:15]=[C:14]4[C:19]([F:22])([F:21])[F:20])=[CH:7][CH:8]=2)[CH:3]=[CH:2]1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 109883732,4-Dichlorobenzyl bromideHCID 86603023HCID 86603023, compound

Product 1

HCID 86603022HCID 86603022, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 3-(1H-indol-5-yl)-2-(2,4,6-trifluorobenzyl)-7-(trifluoromethyl)-2H-indazole (0.025 g, 0.056 mmol) and sodium hydride (60% in oil, 0.003 g, 0.07 mmol) in 1 mL DMF was stirred at ambient temperature under nitrogen for 20 minutes. 2,4-dichlorobenzyl bromide (0.081 g, 0.42 mmol) was added to the reaction mixture, which was stirred overnight and then partitioned between EtOAc and H2O. The organic phase was concentrated and purified by normal phase HPLC (silica, hexane-EtOAc, 4:1) to provide the title compound.

Workup

  1. custompartitioned between EtOAc and H2O
  2. concentrationThe organic phase was concentrated
  3. custompurified by normal phase HPLC (silica, hexane-EtOAc, 4:1)

Sources & evidence

ORD record
ord-f06b3c35ea004e2b889ae7b05e0830ea
Source dataset
uspto-grants-2009_09
Patent number
US07592363B2

Reaction notes

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