Aluminium lithium hydride → (4-(Benzyloxy)-6-chloropyrazolo[1,5-a]pyridin-3-yl)methanol

HRID 2209240Notes

Reaction equation

HRID 2209240 reaction equation
[CH2:1]([O:8][C:9]1[C:10]2[N:11]([N:16]=[CH:17][C:18]=2[C:19](OC)=[O:20])[CH:12]=[C:13]([Cl:15])[CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[CH2:1]([O:8][C:9]1[C:10]2[N:11]([N:16]=[CH:17][C:18]=2[CH2:19][OH:20])[CH:12]=[C:13]([Cl:15])[CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 117843167Methyl 4-(benzyloxy)-6-chloropyrazolo[1,5-a]pyridine-3-carboxylate

Product 1

HCID 117843305(4-(Benzyloxy)-6-chloropyrazolo[1,5-a]pyridin-3-yl)methanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 4-(benzyloxy)-6-chloropyrazolo[1,5-a]pyridine-3-carboxylate (220 mg, 0.692 mmol) in THF (3.0 mL) at 0° C. was added lithium aluminum hydride (0.783 mL, 0.783 mmol, 1M solution in THF). The reaction was warmed to room temperature and was stirred for 30 minutes. The reaction was quenched by the addition of a saturated aqueous solution of KHSO4 and was then diluted with EtOAc. The layers were separated and the aqueous layer was washed with EtOAc several times until no longer cloudy. Combined organics were washed with brine, dried (MgSO4), filtered and concentrated to afford (4-(benzyloxy)-6-chloropyrazolo[1,5-a]pyridin-3-yl)methanol which was used directly in the next reaction. LCMS-ESI+ (m/z): [M+H]+ calcd for C15H13ClN2O2: 289.1; found 289.0.

Workup

  1. customThe reaction was quenched by the addition of a saturated aqueous solution of KHSO4
  2. additionwas then diluted with EtOAc
  3. customThe layers were separated
  4. washthe aqueous layer was washed with EtOAc several times until no longer cloudy
  5. washCombined organics were washed with brine
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-6ce6628b9943497a99fe9b882ba2162d
Source dataset
uspto-grants-2016_06
Patent number
US09376441B2

Reaction notes

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