Sodium borohydride → [6-(1H-pyrazol-1-yl)pyridin-2-yl]methanol

HRID 594257Notes

Reaction equation

HRID 594257 reaction equation
[N:1]1([C:6]2[N:11]=[C:10]([C:12](OC)=[O:13])[CH:9]=[CH:8][CH:7]=2)[CH:5]=[CH:4][CH:3]=[N:2]1.[BH4-].[Na+]>CCO>[N:1]1([C:6]2[N:11]=[C:10]([CH2:12][OH:13])[CH:9]=[CH:8][CH:7]=2)[CH:5]=[CH:4][CH:3]=[N:2]1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 69083337methyl 6-(1H-pyrazol-1-yl)picolinate

Product 1

HCID 62255710[6-(1H-pyrazol-1-yl)pyridin-2-yl]methanol

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of methyl 6-(1H-pyrazol-1-yl)picolinate (476 mg; 2.34 mmol) in anh. EtOH (10 ml) was treated with NaBH4 (443 mg; 11.71 mmol), and the resulting mixture was stirred at rt, under nitrogen, for 16 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=20/1) afforded (6-(1H-pyrazol-1-yl)pyridin-2-yl)methanol as a colorless oil. LC-MS (conditions A): tR=0.45 min.; [M+H]+: 176.11 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=20/1)

Sources & evidence

ORD record
ord-d7b4b80dd7704ef3b67d027a57c261bc
Source dataset
uspto-grants-2016_01
Patent number
US09242970B2

Reaction notes

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