Aluminium lithium hydride → HCID 22100917, compound

HRID 1458337Notes

Reaction equation

HRID 1458337 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]2[NH:12][C:13]3[C:18]([C:19]=2[CH2:20][CH2:21][NH:22][C:23](=O)[CH2:24][CH2:25][C:26]2[CH:27]=[C:28]4[C:32](=[CH:33][CH:34]=2)[NH:31][CH:30]=[CH:29]4)=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].[H-].[Al+3].[Li+].[H-].[H-].[H-]>O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]2[NH:12][C:13]3[C:18]([C:19]=2[CH2:20][CH2:21][NH:22][CH2:23][CH2:24][CH2:25][C:26]2[CH:27]=[C:28]4[C:32](=[CH:33][CH:34]=2)[NH:31][CH:30]=[CH:29]4)=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 22100913HCID 22100913, compound

Product 1

HCID 22100917HCID 22100917, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
77 °C

Procedure

To a solution of N-{2-[2-(3,4-dimethoxyphenyl)-1H-indol-3-yl]ethyl}-3-(1H-indol-5-yl)propionamide (60 mg in 2.0 mL dry tetrahydrofuran) at 0° C. was added 26 mg lithium aluminum hydride and the mixture heated to 77° C. on an oil bath. After 5.5 hours, the mixture was cooled to 0° C. and quenced by the addition of 0.025 mL water and stirred vigorously for 30 minutes at which time the suspension was filtered through a pad of sodium sulfate and the filtrate concentated in vacuo. Purification by flash chromatography (methylene chloride:methanol, 92:8) gave the title compound (32 mg). m/e=454 (M+H)

Workup

  1. temperaturethe mixture was cooled to 0° C.
  2. filtrationwas filtered through a pad of sodium sulfate
  3. customPurification by flash chromatography (methylene chloride:methanol, 92:8)

Sources & evidence

ORD record
ord-d40ac887ba1745388e54d18fb49e37eb
Source dataset
uspto-grants-1998_12
Patent number
US05849764

Reaction notes

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