Water → HCID 66926158, compound

HRID 2170790Notes

Reaction equation

HRID 2170790 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:12]=[C:11]([CH3:13])[NH:10][N:9]=2)=[CH:4][CH:3]=1.[H-].[Na+].[CH3:16][O:17][C:18](=[O:25])[CH2:19][CH2:20][C:21](=[O:24])[CH2:22]Br.O>CN(C)C=O>[CH3:16][O:17][C:18](=[O:25])[CH2:19][CH2:20][C:21](=[O:24])[CH2:22][N:10]1[C:11]([CH3:13])=[CH:12][C:8]([C:5]2[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=2)=[N:9]1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 60609417629-27-5HCID 9855825Methyl 5-bromo-4-oxopentanoate

Product 1

HCID 66926158HCID 66926158, compoundYield 59.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3-(4-Chloro-phenyl)-5-methyl-1H-pyrazole (1.84 g, 9.6 mmol) was dissolved in dimethylformamide (20 ml) followed by the addition of sodium hydride (60% dispersion in oil, 384 mg, 9.6 mmol). The reaction was stirred at room temperature for 15 min, followed by the addition of 5-bromo-4-oxo-pentanoic acid methyl ester (2 g, 9.6 mmol). The reaction was stirred at room temperature for a further 30 min, before the addition of water (200 ml). The solution was then extracted with ethyl acetate (2×150 ml). The organics were dried over magnesium sulfate and concentrated in vacuo. The crude product was then purified by column chromatography (120g column, DCM to 90% DCM/EtOAc over 50 mins) to give 5-[3-(4-chloro-phenyl)-5-methyl-pyrazol-1-yl]-4-oxo-pentanoic acid methyl ester (1.84 g).

Workup

  1. extractionThe solution was then extracted with ethyl acetate (2×150 ml)
  2. dry with materialThe organics were dried over magnesium sulfate
  3. concentrationconcentrated in vacuo
  4. customThe crude product was then purified by column chromatography (120g column, DCM to 90% DCM/EtOAc over 50 mins)

Sources & evidence

ORD record
ord-91e14560a5134c40aaebb5f997b97ad1
Source dataset
uspto-grants-2015_06
Patent number
US09051300B2

Reaction notes

Loading…