Aluminium lithium hydride → HCID 22100890, compound

HRID 1458378Notes

Reaction equation

HRID 1458378 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([C:9]2[NH:10][C:11]3[C:16]([C:17]=2[CH2:18][CH2:19][NH:20][CH2:21][CH2:22][CH2:23][CH2:24][C:25]2[CH:30]=[CH:29][N:28]=[CH:27][CH:26]=2)=[CH:15][C:14]([C:31](=[O:33])[CH3:32])=[CH:13][CH:12]=3)[CH:5]=[C:6]([CH3:8])[CH:7]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[CH3:1][C:2]1[CH:3]=[C:4]([C:9]2[NH:10][C:11]3[C:16]([C:17]=2[CH2:18][CH2:19][NH:20][CH2:21][CH2:22][CH2:23][CH2:24][C:25]2[CH:26]=[CH:27][N:28]=[CH:29][CH:30]=2)=[CH:15][C:14]([CH:31]([OH:33])[CH3:32])=[CH:13][CH:12]=3)[CH:5]=[C:6]([CH3:8])[CH:7]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 22100898HCID 22100898, compound

Product 1

HCID 22100890HCID 22100890, compoundYield 88.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1-{2-(3,5-dimethylphenyl)-3-[2-(4-pyridin-4-yl-butylamino)ethyl]-1H-indol-5-yl}ethanone (45 mg in 2 mL dry tetrahydrofuran) at 0° C. was added 0.30 mL of a 1M solution of lithium aluminum hydride in tetrahydrofuran and the mixture stirred at low temperature. After 45 minutes, the reaction was quenched by the addition of saturated aqueous ammonium chloride and the mixture extracted with ethyl acetate. The organic portion was washed with brine, dried over sodium sulfate and purified by flash chromatography on silica gel (methylene chloride:methanol:ammonium hydroxide, 90:10:0.25) to give the title compound (40 mg). m/e=442 (M+H).

Workup

  1. customthe reaction was quenched by the addition of saturated aqueous ammonium chloride
  2. extractionthe mixture extracted with ethyl acetate
  3. washThe organic portion was washed with brine
  4. dry with materialdried over sodium sulfate
  5. custompurified by flash chromatography on silica gel (methylene chloride:methanol:ammonium hydroxide, 90:10:0.25)

Sources & evidence

ORD record
ord-68dca4250e9b4c689d572f063d12e3d2
Source dataset
uspto-grants-1998_12
Patent number
US05849764

Reaction notes

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