Pyridinium → HCID 58268559, compound

HRID 1517601Notes

Reaction equation

HRID 1517601 reaction equation
[CH:1]1([C:4]2[C:5]([N:10]3[CH:14]=[C:13]([CH2:15][OH:16])[C:12]([CH3:17])=[N:11]3)=[N:6][CH:7]=[CH:8][CH:9]=2)[CH2:3][CH2:2]1.[NH+]1C=CC=CC=1>ClCCl>[CH:1]1([C:4]2[C:5]([N:10]3[CH:14]=[C:13]([CH:15]=[O:16])[C:12]([CH3:17])=[N:11]3)=[N:6][CH:7]=[CH:8][CH:9]=2)[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 4989215PyridiniumHCID 67169028HCID 67169028, compound

Product 1

HCID 58268559HCID 58268559, compoundYield 20%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of [1-(3-cyclopropyl-pyridin-2-yl)-3-methyl-pyrazol-4-yl]-methanol (1.1 g, 5.0 mmol) in dry dichloromethane (15 mL) is added pyridinium chlorocromate (1.2 g, 5.5 mmol) under nitrogen atmosphere. The reaction mixture is stirred at room temperature for 2 h and then filtered through celite. The filtrate is concentrated under reduced pressure. The crude mixture is purified on silica gel eluting with hexane/ethyl acetate (90:10, 80:20) to yield 0.2 g (20%) of the title compound. MS (m/z): 228 (M+1).

Workup

  1. filtrationfiltered through celite
  2. concentrationThe filtrate is concentrated under reduced pressure
  3. customThe crude mixture is purified on silica gel eluting with hexane/ethyl acetate (90:10, 80:20)

Sources & evidence

ORD record
ord-84a289f71ec24378af77e30e5b41714e
Source dataset
uspto-grants-2012_07
Patent number
US08232289B2

Reaction notes

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