Aluminium lithium hydride → HCID 67184148, compound

HRID 45829Notes

Reaction equation

HRID 45829 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[N:7]1[CH:12]=[CH:11][C:10]([C:13]2[C:14]([C:26]3[CH:27]=[C:28]([CH:31]=[CH:32][CH:33]=3)[C:29]#[N:30])=[N:15][N:16]([CH2:18][O:19][CH2:20][CH2:21][Si:22]([CH3:25])([CH3:24])[CH3:23])[CH:17]=2)=[CH:9][CH:8]=1>C1COCC1>[N:7]1[CH:8]=[CH:9][C:10]([C:13]2[C:14]([C:26]3[CH:27]=[C:28]([CH:31]=[CH:32][CH:33]=3)[CH2:29][NH2:30])=[N:15][N:16]([CH2:18][O:19][CH2:20][CH2:21][Si:22]([CH3:25])([CH3:23])[CH3:24])[CH:17]=2)=[CH:11][CH:12]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 67184530HCID 67184530, compound

Product 1

HCID 67184148HCID 67184148, compoundYield 57.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Lithium aluminium hydride (1 M in THF, 68.2 mmol, 10 eq) was added to a solution of 3-[4-pyridin-4-yl-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrazol-3-yl]-benzonitrile (2.57 g, 6.82 mmol) in dry THF (45.0 mL) under nitrogen and the reaction mixture was stirred at reflux for 3 hours. The reaction was cooled down in an ice bath and distilled water was added dropwise followed by a 1M NaOH solution (7.5 ml). The organic layer was removed under vacuum and DCM was added (30 ml) to the water phase. The dichloromethane layer was washed with brine and dried over Na2SO4. The filtrate was evaporated to dryness to give an oil, which was purified over silica gel, using DCM/MeOH/NH4OH (9.8:0.2:0.05) as eluent, to afford 3-[4-pyridin-4-yl-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrazol-3-yl]-benzylamine (1.48 g, 3.90 mmol, 56%).

Workup

  1. temperatureat reflux for 3 hours
  2. temperatureThe reaction was cooled down in an ice bath
  3. distillationdistilled water
  4. additionwas added dropwise
  5. customThe organic layer was removed under vacuum and DCM
  6. additionwas added (30 ml) to the water phase
  7. washThe dichloromethane layer was washed with brine
  8. dry with materialdried over Na2SO4
  9. customThe filtrate was evaporated to dryness
  10. customto give an oil, which
  11. customwas purified over silica gel

Sources & evidence

ORD record
ord-7d910193e5a04f1c96754c5e5c4c6326
Source dataset
uspto-grants-2013_09
Patent number
US08541575B2

Reaction notes

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