Sodium borohydride → (2-(1H-Pyrazol-1-YL)pyridin-4-YL)methanol

HRID 594254Notes

Reaction equation

HRID 594254 reaction equation
[N:1]1([C:6]2[CH:7]=[C:8]([CH:13]=[CH:14][N:15]=2)[C:9](OC)=[O:10])[CH:5]=[CH:4][CH:3]=[N:2]1.[BH4-].[Na+]>CCO>[N:1]1([C:6]2[CH:7]=[C:8]([CH2:9][OH:10])[CH:13]=[CH:14][N:15]=2)[CH:5]=[CH:4][CH:3]=[N:2]1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 690832694-Pyridinecarboxylic acid, 2-(1H-pyrazol-1-yl)-, methyl ester

Product 1

HCID 61256684(2-(1H-Pyrazol-1-YL)pyridin-4-YL)methanol

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of methyl 2-(1H-pyrazol-1-yl)isonicotinate (399 mg; 1.96 mmol) in anh. EtOH (8 ml) was treated with NaBH4 (371 mg; 9.83 mmol), and the resulting mixture was stirred at rt, under nitrogen, for 17 h. After concentration to dryness under reduced pressure, the resulting residue was treated with water, and extracted with DCM. The organic layer was then dried over anh. MgSO4, filtered, and concentrated to dryness under reduced pressure. Purification by FC (DCM/MeOH=25/1) afforded (2-(1H-pyrazol-1-yl)pyridin-4-yl)methanol as a colorless solid. LC-MS (conditions A): tR=0.44 min.; [M+H]+: 176.10 g/mol.

Workup

  1. concentrationAfter concentration to dryness under reduced pressure
  2. additionthe resulting residue was treated with water
  3. extractionextracted with DCM
  4. dry with materialThe organic layer was then dried over anh. MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated to dryness under reduced pressure
  7. customPurification by FC (DCM/MeOH=25/1)

Sources & evidence

ORD record
ord-0ac848958f2845d78d709bba89d69ba7
Source dataset
uspto-grants-2016_01
Patent number
US09242970B2

Reaction notes

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