tert-Butyl methyl ether → ethyl 3-(bromoacetyl)-1-(3-chloropyridin-2-yl)-1H-pyrazole-5-carboxylate

HRID 1630661Notes

Reaction equation

HRID 1630661 reaction equation
[C:1]([C:4]1[CH:8]=[C:7]([C:9]([O:11][CH2:12][CH3:13])=[O:10])[N:6]([C:14]2[C:19]([Cl:20])=[CH:18][CH:17]=[CH:16][N:15]=2)[N:5]=1)(=[O:3])[CH3:2].O1CCOCC1.C(OC)(C)(C)C.[Br:33]Br>O>[Br:33][CH2:2][C:1]([C:4]1[CH:8]=[C:7]([C:9]([O:11][CH2:12][CH3:13])=[O:10])[N:6]([C:14]2[C:19]([Cl:20])=[CH:18][CH:17]=[CH:16][N:15]=2)[N:5]=1)=[O:3]

Participants

6

Reactant 4

HCID 15413tert-Butyl methyl etherHCID 24408BromineHCID 312751,4-DioxaneHCID 66587473ethyl 3-acetyl-1-(3-chloropyridin-2-yl)-1H-pyrazole-5-carboxylate

Product 1

HCID 86661386ethyl 3-(bromoacetyl)-1-(3-chloropyridin-2-yl)-1H-pyrazole-5-carboxylate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

1.20 g (4.40 mmol) of ethyl 3-acetyl-1-(3-chloropyridin-2-yl)-1H-pyrazole-5-carboxylate were initially charged in in each case 30 ml of dioxane and methyl tert-butyl ether and 776 mg (4.85 mmol) of bromine were added dropwise at RT. The mixture was then stirred under reflux for 6 h. The reaction mixture was added to water, and the organic phase was separated off, dried over sodium sulphate and concentrated. The residue was recrystallized from methyl tert-butyl ether.

Workup

  1. additionwere added dropwise at RT
  2. temperatureunder reflux for 6 h
  3. customthe organic phase was separated off
  4. dry with materialdried over sodium sulphate
  5. concentrationconcentrated
  6. customThe residue was recrystallized from methyl tert-butyl ether

Sources & evidence

ORD record
ord-9378d0a888894f969763d0eaa51dcc3b
Source dataset
uspto-grants-2014_07
Patent number
US08791139B2

Reaction notes

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