Water → 1-[5-(5-Chloro-thiophen-2-yl)-isoxazol-3-ylmethyl]-1H-pyrazole-3,5-dicarboxylic acid dimethyl ester

HRID 33242

Reaction equation

HRID 33242 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[CH:10]=[C:9]([C:11]([O:13][CH2:14]C)=[O:12])[NH:8][N:7]=1)=[O:5])C.[H-].[Na+].Br[CH2:19][C:20]1[CH:24]=[C:23]([C:25]2[S:26][C:27]([Cl:30])=[CH:28][CH:29]=2)[O:22][N:21]=1.O>CN(C=O)C>[CH3:14][O:13][C:11]([C:9]1[CH:10]=[C:6]([C:4]([O:3][CH3:1])=[O:5])[N:7]([CH2:19][C:20]2[CH:24]=[C:23]([C:25]3[S:26][C:27]([Cl:30])=[CH:28][CH:29]=3)[O:22][N:21]=2)[N:8]=1)=[O:12]

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 142184diethyl 1H-pyrazole-3,5-dicarboxylateHCID 111501463-Bromomethyl-5-(5-chloro-thiophen-2-yl)-isoxazole

Product 1

HCID 602079511-[5-(5-Chloro-thiophen-2-yl)-isoxazol-3-ylmethyl]-1H-pyrazole-3,5-dicarboxylic acid dimethyl ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 1 g 1H-Pyrazole-3,5-dicarboxylic acid diethyl ester in 20 ml of DMF and 188 mg of sodium hydride (60% in mineral oil) were added at RT. After stirring for 20 min at room temperature 1.32 g of 3-bromomethyl-5-(5-chloro-thiophen-2-yl)-isoxazole were added. The reaction was stirred at room temperature for 3 h. Then 100 ml water were added and the precipitating product was collected by filtration. Yield: 1.7 g.

Workup

  1. additionwere added
  2. filtrationthe precipitating product was collected by filtration

Sources & evidence

ORD record
ord-ac6f8b5ce4bf4aab908a7d48d79f7d5c
Source dataset
uspto-grants-2008_09
Patent number
US07429581B2

Linked notes

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