Aluminium lithium hydride → N-Methyl-[3-phenyl-3-(1H-pyrrolo[2,3-b]pyridin-3-yl)-propyl]amine

HRID 1869184Notes

Reaction equation

HRID 1869184 reaction equation
[CH3:1][NH:2][C:3](=O)[CH2:4][CH:5]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:6]1[C:14]2[C:9](=[N:10][CH:11]=[CH:12][CH:13]=2)[NH:8][CH:7]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[CH3:1][NH:2][CH2:3][CH2:4][CH:5]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:6]1[C:14]2[C:9](=[N:10][CH:11]=[CH:12][CH:13]=2)[NH:8][CH:7]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydride2×HCID 68552631HCID 68552631, compound

Product 1

HCID 16725756N-Methyl-[3-phenyl-3-(1H-pyrrolo[2,3-b]pyridin-3-yl)-propyl]amineYield 56%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a RT suspension of N-methyl-3-phenyl-3-(1H-pyrrolo[2,3-b]pyridin-3-yl)-propionamide (54 mg, 0.19 mmol) in THF (5 ml) was added LiAlH4 (0.38 ml, 1M in THF) at room temperature. The resulting mixture was refluxed for 4 h, then the same amount of LiAlH4 was added. The resulting mixture was refluxed overnight, cooled to RT, quenched by addition of Na2SO4.10H2O. The mixture was stirred for 30 min and the solid was filtered off and washed with EtOAc. The filtrate was concentrated and purified via flash chromatography (DCM/MeOH/NH4OH) affording N-Methyl-[3-phenyl-3-(1H-pyrrolo[2,3-b]pyridin-3-yl)-propyl]amine as a white foam (28 mg, 56% yield); MS M+H=266.

Workup

  1. temperatureThe resulting mixture was refluxed for 4 h
  2. temperatureThe resulting mixture was refluxed overnight
  3. customquenched by addition of Na2SO4.10H2O
  4. filtrationthe solid was filtered off
  5. washwashed with EtOAc
  6. concentrationThe filtrate was concentrated
  7. custompurified via flash chromatography (DCM/MeOH/NH4OH)

Sources & evidence

ORD record
ord-3db3c3e87788460abb8aeeecf7d955aa
Source dataset
uspto-grants-2009_12
Patent number
US07638517B2

Reaction notes

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