Water → HCID 23025094, compound

HRID 350207Notes

Reaction equation

HRID 350207 reaction equation
[OH:1][C:2]1[C:6]([CH2:7][CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:5][N:4]([CH2:14][C:15]2[CH:20]=[CH:19][C:18]([OH:21])=[CH:17][CH:16]=2)[N:3]=1.[H-].[Na+].[N:24]1[CH:29]=[CH:28][CH:27]=[C:26]([CH2:30]Cl)[CH:25]=1.O>CN(C)C=O>[N:24]1[CH:29]=[CH:28][CH:27]=[C:26]([CH2:30][O:1][C:2]2[C:6]([CH2:7][CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:5][N:4]([CH2:14][C:15]3[CH:16]=[CH:17][C:18]([O:21][CH2:30][C:26]4[CH:25]=[N:24][CH:29]=[CH:28][CH:27]=4)=[CH:19][CH:20]=3)[N:3]=2)[CH:25]=1

Participants

6

Reactant 4

HCID 962WaterHCID 183583-(Chloromethyl)pyridineHCID 24758Sodium hydrideHCID 178471112HCID 178471112, compound

Product 1

HCID 23025094HCID 23025094, compoundYield 75.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of ethyl 3-[3-hydroxy-1-(4-hydroxybenzyl)-1H-pyrazol-4-yl]propionate (435 mg) in N,N-dimethylformamide (10 ml), sodium hydride (60%, oily, 120 mg) was added at 0° C., and then the solution was stirred at room temperature for 30 minutes. 3-Picolyl chloride (574 mg) was added to the reaction mixture, which was stirred at room temperature for one hour. The reaction mixture was poured into water, which was extracted with ethyl acetate. The ethyl acetate layer was washed with dilute hydrochloric acid, then, with saturated aqueous sodium chloride solution, and dried (MgSO4) and concentrated. The residue was subjected to silica gel column chromatography, and ethyl 3-[3-(3-pyridylmethoxy)-1-[4-(3-pyridylmethoxy)benzyl]-1H-pyrazol-4-yl]propionate (533 mg, yield: 75%) was obtained as a colorless oily substance from the fraction eluted with ethyl acetate.

Workup

  1. stirringwas stirred at room temperature for one hour
  2. extractionwas extracted with ethyl acetate
  3. washThe ethyl acetate layer was washed with dilute hydrochloric acid
  4. dry with materialwith saturated aqueous sodium chloride solution, and dried (MgSO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-49e8fa1717734562b6b908810aa04d9a
Source dataset
uspto-grants-2007_02
Patent number
US07179823B1

Reaction notes

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