Water → ethyl [1-[6-[2-(2-furyl)-5-methyl-4-oxazolylmethoxy]-3-pyridylmethyl]-3-phenyl-1H-pyrazol-4-yl]acetate

HRID 350302Notes

Reaction equation

HRID 350302 reaction equation
[H-].[Na+].Cl[CH2:4][C:5]1[CH:6]=[CH:7][C:8]([O:11][CH2:12][C:13]2[N:14]=[C:15]([C:19]3[O:20][CH:21]=[CH:22][CH:23]=3)[O:16][C:17]=2[CH3:18])=[N:9][CH:10]=1.[CH2:24]([O:26][C:27](=[O:40])[CH2:28][C:29]1[C:30]([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)=[N:31][NH:32][CH:33]=1)[CH3:25].O>CN(C)C=O>[O:20]1[CH:21]=[CH:22][CH:23]=[C:19]1[C:15]1[O:16][C:17]([CH3:18])=[C:13]([CH2:12][O:11][C:8]2[N:9]=[CH:10][C:5]([CH2:4][N:32]3[CH:33]=[C:29]([CH2:28][C:27]([O:26][CH2:24][CH3:25])=[O:40])[C:30]([C:34]4[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=4)=[N:31]3)=[CH:6][CH:7]=2)[N:14]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 230763795-Chloromethyl-2-[2-(2-furyl)-5-methyl-4-oxazolylmethoxy]pyridineHCID 178470745HCID 178470745, compound

Product 1

HCID 86760435ethyl [1-[6-[2-(2-furyl)-5-methyl-4-oxazolylmethoxy]-3-pyridylmethyl]-3-phenyl-1H-pyrazol-4-yl]acetateYield 67%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (60%, oily, 70.0 mg) was added to a solution of 5-chloromethyl-2-[2-(2-furyl)-5-methyl-4-oxazolylmethoxy]pyridine (533 mg) and ethyl(3-phenyl-1H-pyrazol-4-yl)acetate (403 mg) in N,N-dimethylformamide (10 ml) at 0° C., and the mixture was stirred at room temperature for 1 hour. The reaction mixture was poured into water, and extracted with ethyl acetate. The ethyl acetate layer was washed with saturated aqueous sodium chloride solution, dried (MgSO4), and concentrated. The residue was subjected to silica gel column chromatography to obtain ethyl [1-[6-[2-(2-furyl)-5-methyl-4-oxazolylmethoxy]-3-pyridylmethyl]-3-phenyl-1H-pyrazol-4-yl]acetate (581 mg, yield: 67%) as a colorless oily substance from the fraction eluted with ethyl acetate-hexane (1:1, volume ratio).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe ethyl acetate layer was washed with saturated aqueous sodium chloride solution
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-d5907e7393bc4ea0b763e55fcd81e60d
Source dataset
uspto-grants-2007_02
Patent number
US07179823B1

Reaction notes

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