Aluminium lithium hydride → HCID 57985892, compound

HRID 1869192Notes

Reaction equation

HRID 1869192 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][N:6]=[C:5]2[NH:9][CH:10]=[C:11]([CH:12]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[CH2:13][C:14]([NH:16][CH3:17])=O)[C:4]=12.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][N:6]=[C:5]2[NH:9][CH:10]=[C:11]([CH:12]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[CH2:13][CH2:14][NH:16][CH3:17])[C:4]=12

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 57985914HCID 57985914, compound

Product 1

HCID 57985892HCID 57985892, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a RT suspension of 3-(4-methoxy-1H-pyrrolo[2,3-b]pyridin-3-yl)-N-methyl-3-phenyl-propionamide (155 mg, 0.50 mmol) in THF (5 mL) was slowly added LAH (1 M in THF, 1.5 mmol). The mixture was refluxed overnight, cooled to RT, and quenched by addition of freshly ground Na2SO4.10H2O. After stirring for 20 min, the solid was filtered off and washed with EtOAc (10 mL, 3 times) and DCM (10 mL, 2 times). The filtrate was concentrated, and the residue was purified via flash chromatography (DCM/MeOH/NH4OH) to afford [3-(4-Methoxy-1H-pyrrolo[2,3-b]pyridin-3-yl)-3-phenyl-propyl]-methyl-amine as a white solid (90 mg, 61% yield).

Workup

  1. temperatureThe mixture was refluxed overnight
  2. customquenched by addition of freshly ground Na2SO4.10H2O
  3. filtrationthe solid was filtered off
  4. washwashed with EtOAc (10 mL, 3 times) and DCM (10 mL, 2 times)
  5. concentrationThe filtrate was concentrated
  6. customthe residue was purified via flash chromatography (DCM/MeOH/NH4OH)

Sources & evidence

ORD record
ord-644b83b1d3494499b50b4b557d8dff38
Source dataset
uspto-grants-2009_12
Patent number
US07638517B2

Reaction notes

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