HCID 21090883, compound → HCID 21090884, compound

HRID 351272Notes

Reaction equation

HRID 351272 reaction equation
[CH3:1][O:2][C:3]1[N:8]=[CH:7][C:6]([N:9]2[C:13]([C:14]3[CH:21]=[CH:20][C:17]([C:18]#[N:19])=[CH:16][CH:15]=3)=[CH:12][C:11]([O:22][CH2:23][C:24]([F:27])([F:26])[F:25])=[N:10]2)=[CH:5][CH:4]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[CH3:1][O:2][C:3]1[N:8]=[CH:7][C:6]([N:9]2[C:13]([C:14]3[CH:15]=[CH:16][C:17]([CH2:18][NH2:19])=[CH:20][CH:21]=3)=[CH:12][C:11]([O:22][CH2:23][C:24]([F:27])([F:25])[F:26])=[N:10]2)=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 21090883HCID 21090883, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 21090884HCID 21090884, compoundYield 100.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-[1-(6-methoxy-3-pyridinyl)-3-(2,2,2-trifluoroethoxy)-1-H-pyrazol-5-yl]benzonitrile (197 mg) in THF (2 ml) was added lithium aluminum hydride (30 mg) under ice-bath cooling. The mixture was stirred at same temperature for 1 hour and then at ambient temperature for 2 hours. The reaction was quenched by adding 5% aqueous solution of potassium sodium tartaric acid (ca. 0.5 ml) . The mixture was diluted with AcOEt, dried over MgSO4, and filtered through a celite pad. The filtrate was concentrated in vacuo to give {4-[1-(6-methoxy-3-pyridinyl)-3-(2,2,2-trifluoro-ethoxy)-1-H-pyrazol-5-yl]benzyl}amine (200 mg) as an oil.

Workup

  1. temperaturecooling
  2. waitat ambient temperature for 2 hours
  3. customThe reaction was quenched
  4. additionby adding 5% aqueous solution of potassium sodium tartaric acid (ca. 0.5 ml)
  5. additionThe mixture was diluted with AcOEt
  6. dry with materialdried over MgSO4
  7. filtrationfiltered through a celite pad
  8. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-6dd6d3f4942741cc8408662b73cb3273
Source dataset
uspto-grants-2007_02
Patent number
US07183306B2

Reaction notes

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