Lithium aluminum hydride → 2-ethyl-5-(4-fluoro-benzylamino)-2H-pyrazole-3-carbaldehyde

HRID 1024237Notes

Reaction equation

HRID 1024237 reaction equation
C[O:2][C:3]([C:5]1[N:6]([CH2:19][CH3:20])[N:7]=[C:8]([NH:10][CH2:11][C:12]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=2)[CH:9]=1)=O.[AlH4-].[Li+].O.O.O.O.O.O.O.O.O.O.S([O-])([O-])(=O)=O.[Na+].[Na+]>O1CCCC1>[CH2:19]([N:6]1[C:5]([CH:3]=[O:2])=[CH:9][C:8]([NH:10][CH2:11][C:12]2[CH:13]=[CH:14][C:15]([F:18])=[CH:16][CH:17]=2)=[N:7]1)[CH3:20]

Participants

5

Reactant 3

HCID 28112Lithium aluminum hydrideHCID 62649Sodium sulfate decahydrateHCID 576193832-ethyl-5-(4-fluoro-benzylamino)-2H-pyrazole-3-carboxylic acid methyl ester

Product 1

HCID 576192072-ethyl-5-(4-fluoro-benzylamino)-2H-pyrazole-3-carbaldehyde

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 2-ethyl-5-(4-fluoro-benzylamino)-2H-pyrazole-3-carboxylic acid methyl ester (529, 1.00 g, 3.61 mol) in tetrahydrofuran (70.0 mL) under an atmosphere of nitrogen at room temperature, lithium tetrahydroaluminate (1.00M of in tetrahydrofuran, 10.00 mL) was slowly added. The reaction was stirred at room temperature overnight, followed by slowly adding sodium sulfate decahydrate (15.0 g). After 2 hours, the reaction was filtered, concentrated and purified with silica gel column chromatography eluting with 20% to 100% ethyl acetate in hexane to give a yellow oil (530, 0.16 g, 18%). MS (ESI) [M+H+]+=248.2.

Workup

  1. waitAfter 2 hours
  2. filtrationthe reaction was filtered
  3. concentrationconcentrated
  4. custompurified with silica gel column chromatography
  5. washeluting with 20% to 100% ethyl acetate in hexane
  6. customto give a yellow oil (530, 0.16 g, 18%)

Sources & evidence

ORD record
ord-2ec8cc02916049519ebe2b8aa35242ce
Source dataset
uspto-grants-2014_05
Patent number
US08722702B2

Reaction notes

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