Sodium Iodide → 1h-Indazole-1-carboxylic acid,3-(3-fluorophenyl)-5-(iodomethyl)-,1,1-dimethylethyl ester

HRID 503135Notes

Reaction equation

HRID 503135 reaction equation
Cl[CH2:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[N:8]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[N:7]=[C:6]2[C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([F:25])[CH:20]=1.[I-:26].[Na+]>CC(C)=O>[F:25][C:21]1[CH:20]=[C:19]([C:6]2[C:5]3[C:9](=[CH:10][CH:11]=[C:3]([CH2:2][I:26])[CH:4]=3)[N:8]([C:12]([O:14][C:15]([CH3:17])([CH3:16])[CH3:18])=[O:13])[N:7]=2)[CH:24]=[CH:23][CH:22]=1

Participants

4

Reactant 2

HCID 5238Sodium IodideHCID 222606161h-Indazole-1-carboxylic acid,5-(chloromethyl)-3-(3-fluorophenyl)-,1,1-dimethylethyl ester

Product 1

HCID 222610741h-Indazole-1-carboxylic acid,3-(3-fluorophenyl)-5-(iodomethyl)-,1,1-dimethylethyl esterYield 101.8%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 500 mg of tert-butyl 5-(chloromethyl)-3-(3-fluorophenyl)-1H-1-indazolecarboxylate produced in Production Example I-24-b in 2.5 ml acetone was added 218 mg of sodium iodide, and the mixture was stirred at room temperature for 2 hours. After filtering off the resulting sodium chloride through Celite, the solvent was evaporated, to give 638 mg of the title compound as bright yellow crystals.

Workup

  1. filtrationAfter filtering off the resulting sodium chloride through Celite
  2. customthe solvent was evaporated

Sources & evidence

ORD record
ord-04f9217a15684deea4cc46edc4bd7c94
Source dataset
uspto-grants-2010_08
Patent number
US07776890B2

Reaction notes

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