Acetic Acid → 2-(4-Benzyloxy-phenyl-2H-pyrazol-3-yl]-pyridine

HRID 33874

Reaction equation

HRID 33874 reaction equation
[C:1](O)(=O)[CH3:2].Cl.[CH2:6]([O:13][C:14]1[CH:19]=[CH:18][C:17]([NH:20][NH2:21])=[CH:16][CH:15]=1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.C(=O)(O)[O-].[Na+]>CO>[CH2:6]([O:13][C:14]1[CH:15]=[CH:16][C:17]([N:20]2[C:8]([C:1]3[CH:2]=[CH:15][CH:16]=[CH:17][N:20]=3)=[CH:7][CH:6]=[N:21]2)=[CH:18][CH:19]=1)[C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 516892Sodium BicarbonateHCID 3016725(4-(Benzyloxy)phenyl)hydrazine monohydrochloride

Product 1

HCID 866064162-(4-Benzyloxy-phenyl-2H-pyrazol-3-yl]-pyridine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 3-Dimethylamino-1-pyridin-4-yl-propenone (590 mg) in methanol (10 ml) was added acetic acid (0.5 ml) and (4-Benzyloxy-phenyl)-hydrazine hydrogen chloride (836 mg) and the reaction mixture heated to 60° C. for 6 h. The reaction mixture was poured into saturated sodium bicarbonate, extracted with ethyl acetate, dried magnesium sulfate, filtered and concentrated. Purification via combiflash MPLC provided the title compound (795 mg). MS: (M+H m/z=328.1).

Workup

  1. extractionextracted with ethyl acetate, dried magnesium sulfate
  2. filtrationfiltered
  3. concentrationconcentrated
  4. customPurification via combiflash MPLC

Sources & evidence

ORD record
ord-59dbb7e24d53454c96698a6b1ff946d5
Source dataset
uspto-grants-2008_09
Patent number
US07429665B2

Linked notes

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