Aluminium lithium hydride → (1-(4-methoxy-1H-pyrrolo[2,3-c]pyridin-7-yl)-1H-1,2,4-triazol-3-yl)methanol

HRID 885061Notes

Reaction equation

HRID 885061 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[N:7][C:6]([N:9]2[CH:13]=[N:12][C:11]([C:14](OC)=[O:15])=[N:10]2)=[C:5]2[NH:18][CH:19]=[CH:20][C:4]=12.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[CH3:1][O:2][C:3]1[CH:8]=[N:7][C:6]([N:9]2[CH:13]=[N:12][C:11]([CH2:14][OH:15])=[N:10]2)=[C:5]2[NH:18][CH:19]=[CH:20][C:4]=12

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 58026033methyl 1-(4-methoxy-1H-pyrrolo[2,3-c]pyridin-7-yl)-1H-1,2,4-triazole-3-carboxylate

Product 1

HCID 58026032(1-(4-methoxy-1H-pyrrolo[2,3-c]pyridin-7-yl)-1H-1,2,4-triazol-3-yl)methanolYield 50.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 1-(4-methoxy-1H-pyrrolo[2,3-c]pyridin-7-yl)-1H-1,2,4-triazole-3-carboxylate (220 mg, 0.805 mmol) in THF (20 mL) was added LiAlH4 (1.208 mL, 2.415 mmol) dropwise over 5 min period at room temperature. The solution was refluxed for 1H and then cooled in an ice bath. The reaction mixture was quenched with water and extracted with EtOAc (3×100 ml). The organic layers were combined, washed with brine (30 ml), dried under MgSO4 and concentrated. The residue was purified by prep. HPLC to give (1-(4-methoxy-1H-pyrrolo[2,3-c]pyridin-7-yl)-1H-1,2,4-triazol-3-yl)methanol (100 mg, 0.408 mmol, 50.6% yield). LCMS: m/z 246.2 (M+H)+, 1.36 min (method 8). 1H NMR (500 MHz, MeOD) δ ppm 9.24 (s, 1H) 7.53 (s, 1H) 7.47 (d, J=3.05 Hz, 1H) 6.68 (d, J=2.75 Hz, 1H) 4.84 (s, 2H) 4.03 (s, 3H).

Workup

  1. temperatureThe solution was refluxed for 1H
  2. temperaturecooled in an ice bath
  3. customThe reaction mixture was quenched with water
  4. extractionextracted with EtOAc (3×100 ml)
  5. washwashed with brine (30 ml)
  6. customdried under MgSO4
  7. concentrationconcentrated
  8. customThe residue was purified by prep

Sources & evidence

ORD record
ord-a8f71945c2db4c87ae6c22b29491673f
Source dataset
uspto-grants-2012_08
Patent number
US08242124B2

Reaction notes

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