Aluminium lithium hydride → (1H-Pyrrolo[2,3-b]pyridin-5-yl)methanol

HRID 269488Notes

Reaction equation

HRID 269488 reaction equation
C[O:2][C:3]([C:5]1[CH:6]=[C:7]2[CH:13]=[CH:12][NH:11][C:8]2=[N:9][CH:10]=1)=O.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[NH:11]1[C:8]2=[N:9][CH:10]=[C:5]([CH2:3][OH:2])[CH:6]=[C:7]2[CH:13]=[CH:12]1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 22832049methyl 1H-pyrrolo[2,3-b]pyridine-5-carboxylate

Product 1

HCID 22832050(1H-Pyrrolo[2,3-b]pyridin-5-yl)methanolYield 98%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 1H-Pyrrolo[2,3-b]pyridine-5-carboxylic acid methyl ester (75 mg, 0.394 mmol) in THF at 0 C was added lithium aluminum hydride (45 mg, 1.18 mmol) and the reaction mixture was slowly allowed to warm to ambient temperature. The reaction was refluxed for 12 hr, allowed to cool and quenched with water. Extraction with ethyl acetate, washed with brine, dried (Na2SO4) to afford (1H-Pyrrolo[2,3-b]pyridin-5-yl)-methanol (57 mg, 98% yield).

Workup

  1. temperatureThe reaction was refluxed for 12 hr
  2. temperatureto cool
  3. customquenched with water
  4. extractionExtraction with ethyl acetate
  5. washwashed with brine
  6. dry with materialdried (Na2SO4)

Sources & evidence

ORD record
ord-970f12e663a64fd8a5d51b42c818c26c
Source dataset
uspto-grants-2008_11
Patent number
US07446199B2

Reaction notes

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