Aluminium lithium hydride → HCID 22100887, compound

HRID 1458366Notes

Reaction equation

HRID 1458366 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([C:9]2[NH:10][C:11]3[C:16]([C:17]=2[C:18](=O)[C:19]([N:21]2[CH2:26][CH2:25][CH:24]([C:27]4[CH:32]=[CH:31][N:30]=[CH:29][CH:28]=4)[CH2:23][CH2:22]2)=O)=[CH:15][CH:14]=[CH:13][CH:12]=3)[CH:5]=[C:6]([CH3:8])[CH:7]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[CH3:8][C:6]1[CH:5]=[C:4]([C:9]2[NH:10][C:11]3[C:16]([C:17]=2[CH2:18][CH2:19][N:21]2[CH2:26][CH2:25][CH:24]([C:27]4[CH:28]=[CH:29][N:30]=[CH:31][CH:32]=4)[CH2:23][CH2:22]2)=[CH:15][CH:14]=[CH:13][CH:12]=3)[CH:3]=[C:2]([CH3:1])[CH:7]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 22100931HCID 22100931, compound

Product 1

HCID 22100887HCID 22100887, compoundYield 51.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1-[2-(3,5-dimethylphenyl)-1H-indol-3-yl]-2-(3,4,5,6-tetrahydro-2H-[4,4']bipyridinyl-1-yl)ethane-1,2-dione (148 mg in dry tetrahydrofuran) was added dropwise 2.71 mL of a 1M solution of lithium aluminum hydride in tetrahydrofuran and the mixture heated to reflux on an oil bath. After 1.5 hours the mixture was cooled and quenched by the sequential addition of 30 mL water and 4 mL ammonium hydroxide and 25 mL ethyl acetate. The mixture was filtered to remove the solids. The organic portion was washed with brine, dried over magnesium sulfate and concentrated in vacuo to give the title compound (71 mg). m/e=410 (M+H).

Workup

  1. temperaturethe mixture heated
  2. temperatureto reflux on an oil bath
  3. temperatureAfter 1.5 hours the mixture was cooled
  4. customquenched by the sequential addition of 30 mL water and 4 mL ammonium hydroxide and 25 mL ethyl acetate
  5. filtrationThe mixture was filtered
  6. customto remove the solids
  7. washThe organic portion was washed with brine
  8. dry with materialdried over magnesium sulfate
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-7f79c1b1f3db40bb9b0e099f974f3134
Source dataset
uspto-grants-1998_12
Patent number
US05849764

Reaction notes

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