Aluminium lithium hydride → HCID 68072122, compound

HRID 512053Notes

Reaction equation

HRID 512053 reaction equation
[CH:1]([C:4]1[N:8]2[CH:9]=[C:10]([C:13](OC)=[O:14])[CH:11]=[CH:12][C:7]2=[CH:6][N:5]=1)([CH3:3])[CH3:2].[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[CH:1]([C:4]1[N:8]2[CH:9]=[C:10]([CH2:13][OH:14])[CH:11]=[CH:12][C:7]2=[CH:6][N:5]=1)([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 66667734HCID 66667734, compound

Product 1

HCID 68072122HCID 68072122, compoundYield 59%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To an ice-cold solution of methyl 3-isopropylimidazo[1,5-a]pyridine-6-carboxylate (Preparation 27, 234 mg, 1.07 mmol) in THF (4 mL) was added lithium aluminium hydride solution in THF (2 M, 61 mg, 804 μL, 1.61 mmol). The mixture was allowed to warm to room temperature. After 3 hours the reaction was cooled again in an ice bath and quenched with a saturated solution of sodium sulfate (1 mL). The mixture was stirred for 30 minutes and then filtered through Celite. The filtrate was evaporated to low volume and the aqueous residue extracted with DCM (3×5 mL). The combined organic extracts were washed with brine, dried over magnesium sulfate, filtered and evaporated. The resulting residue was purified by silica gel chromatography eluting with 10 to 100% EtOAc in pentane to yield the title compound as a yellow gum (120 mg, 59%).

Workup

  1. temperatureAfter 3 hours the reaction was cooled again in an ice bath
  2. customquenched with a saturated solution of sodium sulfate (1 mL)
  3. filtrationfiltered through Celite
  4. customThe filtrate was evaporated to low volume
  5. extractionthe aqueous residue extracted with DCM (3×5 mL)
  6. washThe combined organic extracts were washed with brine
  7. dry with materialdried over magnesium sulfate
  8. filtrationfiltered
  9. customevaporated
  10. customThe resulting residue was purified by silica gel chromatography
  11. washeluting with 10 to 100% EtOAc in pentane

Sources & evidence

ORD record
ord-948c0688258d470ba80eba6f3bb10c91
Source dataset
uspto-grants-2015_08
Patent number
US09102621B2

Reaction notes

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