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

HRID 41586Notes

Reaction equation

HRID 41586 reaction equation
Br[C:2]1[CH:7]=[C:6]([CH2:8][OH:9])[CH:5]=[CH:4][N:3]=1.[NH:10]1[CH:14]=[CH:13][CH:12]=[N:11]1.C([O-])([O-])=O.[Cs+].[Cs+]>C(#N)C>[N:10]1([C:2]2[CH:7]=[C:6]([CH2:8][OH:9])[CH:5]=[CH:4][N:3]=2)[CH:14]=[CH:13][CH:12]=[N:11]1

Participants

5

Reactant 3

HCID 1048PyrazoleHCID 10796Cesium carbonateHCID 14512957(2-Bromopyridin-4-yl)methanol

Product 1

HCID 61256684(2-(1H-Pyrazol-1-YL)pyridin-4-YL)methanolYield 74.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of (2-bromopyridin-4-yl)methanol [118289-16-0] (370 mg, 2.00 mmol), 1H-pyrazole (204 mg, 3.00 mmol), Cu powder (26 mg, 0.40 mmol) and Cs2CO3 (1.30 g, 4.00 mmol) in acetonitrile (4 mL) was heated under reflux for 16 h. The reaction mixture was cooled to rt and concentrated under reduced pressure. The residue was taken up in ethyl acetate and washed with water and brine, dried over anhydrous sodium sulfate, filtered and the organic layer was evaporated under reduced pressure. The residue was purified by flash-column chromatography over silicagel (eluent: 50% ethyl acetate in hexane) to yield the title compound (260 mg, 74%). [LCMS RtF=0.31 min, [M+H]+=176.1].

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 16 h
  3. concentrationconcentrated under reduced pressure
  4. washwashed with water and brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. customthe organic layer was evaporated under reduced pressure
  8. customThe residue was purified by flash-column chromatography over silicagel (eluent: 50% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-6340a1b29b894997a58bd6607c698d48
Source dataset
uspto-grants-2013_09
Patent number
US08530648B2

Reaction notes

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