Water → HCID 58408266, compound

HRID 2192280Notes

Reaction equation

HRID 2192280 reaction equation
[CH3:1][C:2]1([CH3:22])[C:10]2[C:5](=[N:6][CH:7]=[C:8]([C:11]3[CH:16]=[CH:15][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:13][CH:12]=3)[CH:9]=2)[NH:4][C:3]1=O.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[O-]S([O-])(=O)=O.[Mg+2]>O1CCCC1>[CH3:1][C:2]1([CH3:22])[C:10]2[C:5](=[N:6][CH:7]=[C:8]([C:11]3[CH:16]=[CH:15][C:14]([C:17]([F:20])([F:18])[F:19])=[CH:13][CH:12]=3)[CH:9]=2)[NH:4][CH2:3]1

Participants

6

Reactant 4

HCID 962WaterHCID 24083Sulfuric acid magnesium salt (1:1)HCID 21226445Aluminium lithium hydride3×HCID 58408278HCID 58408278, compound

Product 1

HCID 58408266HCID 58408266, compoundYield 38.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1.33 g 3,3-Dimethyl-5-(4-trifluoromethyl-phenyl)-1,3-dihydro-pyrrolo[2,3-b]pyridin-2-one were dissolved in 50 ml tetrahydrofuran. 330 mg lithium aluminiumhydride were added and the reaction mixture stirred for one hour at room temperature. Then 330 mg lithium aluminiumhydride were added and the reaction mixture stirred for two hours at room temperature. Then 330 mg lithium aluminiumhydride were added and the reaction mixture stirred for four hours at 50° C. Then 1 ml water was added to the cooled reaction mixture. Then 1 g MgSO4 were added followed by 3 g isolute. The solvent was removed in vacuo and the residue purified by chromatography on silica gel to obtain 490 mg 3,3-Dimethyl-5-(4-trifluoromethyl-phenyl)-2,3-dihydro-1H-pyrrolo[2,3-b]pyridine.

Workup

  1. stirringthe reaction mixture stirred for two hours at room temperature
  2. stirringthe reaction mixture stirred for four hours at 50° C
  3. customThe solvent was removed in vacuo
  4. customthe residue purified by chromatography on silica gel

Sources & evidence

ORD record
ord-41d317fc487f469aa46bd34d1a2720a4
Source dataset
uspto-grants-2012_12
Patent number
US08329725B2

Reaction notes

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