Water → 1-(4-chloro-3-methoxyphenyl)-3-[3-(1,1-dimethylethyl)-1H-pyrazol-1-yl]-2-pyrrolidinone

HRID 721982Notes

Reaction equation

HRID 721982 reaction equation
[CH3:1][C:2]([C:5]1[CH:9]=[CH:8][NH:7][N:6]=1)([CH3:4])[CH3:3].[H-].[Na+].Br[CH:13]1[CH2:17][CH2:16][N:15]([C:18]2[CH:23]=[CH:22][C:21]([Cl:24])=[C:20]([O:25][CH3:26])[CH:19]=2)[C:14]1=[O:27].O>CN(C)C=O>[Cl:24][C:21]1[CH:22]=[CH:23][C:18]([N:15]2[CH2:16][CH2:17][CH:13]([N:7]3[CH:8]=[CH:9][C:5]([C:2]([CH3:4])([CH3:3])[CH3:1])=[N:6]3)[C:14]2=[O:27])=[CH:19][C:20]=1[O:25][CH3:26]

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 21881984HCID 21881984, compoundHCID 178441177HCID 178441177, compound

Product 1

HCID 218819821-(4-chloro-3-methoxyphenyl)-3-[3-(1,1-dimethylethyl)-1H-pyrazol-1-yl]-2-pyrrolidinone

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 3-(1,1-dimethylethyl)-1H-pyrazole (0.22 g, 1.8 mmol) in N,N-dimethylformamide (20 mL) under nitrogen at room temperature was added 60% sodium hydride in mineral oil (79 mg, 2.0 mmol). After the addition, the mixture was stirred at room temperature for ˜15 minutes, and then 3-bromo-1-(4-chloro-3-methoxyphenyl)-2-pyrrolidinone (0.5 g, 1.6 mmol) was added. The resulting reaction mixture was stirred at room temperature overnight and then poured into water (˜100 mL). The aqueous layer was extracted twice with ethyl acetate (˜50 mL each). The organic extracts were combined, washed twice with water (˜100 mL each), dried over MgSO4 and filtered. The filtrate was concentrated. The residue was purified by medium pressure liquid chromatography (silica gel) using as eluant methylene chloride and then 10:1 (by volume) ethyl acetatemethylene chloride to give the title compound, a compound of this invention, as a solid (186 mg) melting at 128–130 ° C.

Workup

  1. additionAfter the addition
  2. customThe resulting reaction mixture
  3. stirringwas stirred at room temperature overnight
  4. extractionThe aqueous layer was extracted twice with ethyl acetate (˜50 mL each)
  5. washwashed twice with water (˜100 mL each)
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationThe filtrate was concentrated
  9. customThe residue was purified by medium pressure liquid chromatography (silica gel)

Sources & evidence

ORD record
ord-f6e69a6c6f26431c9f7a2ad29fdde37b
Source dataset
uspto-grants-2006_11
Patent number
US07138361B2

Reaction notes

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