Dimethylformamide → ethyl 1-[6-(5-methyl-2-phenyl-4-oxazolylmethoxy)-3-pyridylmethyl]-3-phenyl-1H-pyrazole-4-carboxylate

HRID 350313Notes

Reaction equation

HRID 350313 reaction equation
[H-].[Na+].[C:3]1([C:9]2[C:13]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[CH:12][NH:11][N:10]=2)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.Cl[CH2:20][C:21]1[CH:22]=[CH:23][C:24]([O:27][CH2:28][C:29]2[N:30]=[C:31]([C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)[O:32][C:33]=2[CH3:34])=[N:25][CH:26]=1.CN(C)C=O>O>[CH3:34][C:33]1[O:32][C:31]([C:35]2[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=2)=[N:30][C:29]=1[CH2:28][O:27][C:24]1[N:25]=[CH:26][C:21]([CH2:20][N:11]2[CH:12]=[C:13]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[C:9]([C:3]3[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=3)=[N:10]2)=[CH:22][CH:23]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 178328085-Chloromethyl-2-(5-methyl-2-phenyl-4-oxazolyl)methoxypyridineHCID 178469912HCID 178469912, compound

Product 1

HCID 69422789ethyl 1-[6-(5-methyl-2-phenyl-4-oxazolylmethoxy)-3-pyridylmethyl]-3-phenyl-1H-pyrazole-4-carboxylateYield 57%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Sodium hydride (60%, oily, 270 mg) was added to a mixture of ethyl 3-phenyl-1H-pyrazole-4-carboxylate (1.20 g), 5-chloromethyl-2-(5-methyl-2-phenyl-4-oxazolylmethoxy)pyridine (1.75 g), and N,N-dimethylformamide (50 ml) at 0° C., and the mixture was stirred at room temperature for 8 hours. The reaction mixture was poured into water, and extracted with ethyl acetate. The ethyl acetate layer was washed with water, dried (MgSO4), and concentrated. The residue was subjected to silica gel column chromatography to obtain ethyl 1-[6-(5-methyl-2-phenyl-4-oxazolylmethoxy)-3-pyridylmethyl]-3-phenyl-1H-pyrazole-4-carboxylate (1.56 g, yield: 57%) as a colorless oily substance from the fraction eluted with diethyl ether-hexane (2:3, volume ratio).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe ethyl acetate layer was washed with water
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-8e9ca6100ece445287b72a395267972a
Source dataset
uspto-grants-2007_02
Patent number
US07179823B1

Reaction notes

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