Water → Imidazo[1,5-a]pyridin-8-ylmethanol

HRID 1473883Notes

Reaction equation

HRID 1473883 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[NH:7]1[C:11]2[CH:12]=[CH:13]C=NC=2[N:9]=[C:8]1C(OCC)=O.[OH2:21].[OH-].[Na+].[CH2:24]1[CH2:28]O[CH2:26][CH2:25]1>CCOC(C)=O>[CH:26]1[N:9]=[CH:8][N:7]2[CH:11]=[CH:12][CH:13]=[C:24]([CH2:28][OH:21])[C:25]=12

Participants

7

Reactant 5

HCID 962Water2×HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 13353748ethyl 3H-imidazo[4,5-b]pyridine-2-carboxylateHCID 21226445Aluminium lithium hydride

Product 1

HCID 10351843Imidazo[1,5-a]pyridin-8-ylmethanol

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a cold solution of lithium aluminum hydride (1.0 g, 26.3 mmol, 2.0 eq) in THF (40 mL) was added the crude ethyl imidazopyridine carboxylate (2.5 g, 13.2 mmol, 1.0 eq) and the reaction mixture was stirred at rt for 2 h. Reaction was cooled and water (1.7 mL), 15% NaOH (1.7 mL) and water (5.1 mL) were slowly added. Solution was next diluted with excess EtOAc and stirred at rt for 30 min. The solution was filtered and the solid was washed with ethyl acetate. Organic layers were combined, dried and solvent was removed to give crude imidazo[1,5-a]pyridine-8-methanol, which was purified by column chromatography (EtOAc/Hexane). MS: exact mass calculated for C8H8N2O, 148.06; m/z found, 149 [M+H]+.

Workup

  1. customReaction
  2. temperaturewas cooled
  3. stirringstirred at rt for 30 min
  4. filtrationThe solution was filtered
  5. washthe solid was washed with ethyl acetate
  6. customdried
  7. customsolvent was removed

Sources & evidence

ORD record
ord-62aeadd3de064a23bf3ed4c459f1bd6c
Source dataset
uspto-grants-2015_04
Patent number
US09018210B2

Reaction notes

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