Sodium Carbonate → 1-(2-Fluorobenzyl)-3-cyanoindazole

HRID 32314Notes

Reaction equation

HRID 32314 reaction equation
C(=O)([O-])[O-].[Na+].[Na+].[Cl-].[F:8][C:9]1[CH:27]=[CH:26][CH:25]=[CH:24][C:10]=1[CH2:11][N:12]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[C:14]([C:21](N)=[NH2+:22])=[N:13]1.[OH-].[Na+]>C(OCC)(=O)C>[F:8][C:9]1[CH:27]=[CH:26][CH:25]=[CH:24][C:10]=1[CH2:11][N:12]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[C:14]([C:21]#[N:22])=[N:13]1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 14798Sodium HydroxideHCID 114039631-(2-fluorobenzyl)-1H-indazole-3-carboximidamide hydrochloride

Product 1

HCID 113910691-(2-Fluorobenzyl)-3-cyanoindazole

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

2.61 g (24.61 mmol) of sodium carbonate as 10% strength aqueous solution are added to a suspension of 5.00 g (16.41 mmol) of 1-(2-fluorobenzyl)indazole-3-amidinium chloride from Example IIIb) in 100 ml of ethyl acetate, and the mixture is stirred at room temperature for 90 minutes. One molar sodium hydroxide solution is added until the phases have separated. The organic phase is washed with saturated sodium chloride solution, dried over magnesium sulfate and filtered, and the solvent is removed in vacuo. 3.33 g (76% of theory) of the product are obtained.

Workup

  1. customhave separated
  2. washThe organic phase is washed with saturated sodium chloride solution
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. customthe solvent is removed in vacuo
  6. custom3.33 g (76% of theory) of the product are obtained

Sources & evidence

ORD record
ord-4fe2db1f0b6643c7b7b06680043abd4e
Source dataset
uspto-grants-2008_09
Patent number
US07427617B2

Reaction notes

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