Bromine → methyl 4-(bromoacetyl)-1-(3-chloropyridin-2-yl)-1H-pyrrole-2-carboxylate

HRID 874191Notes

Reaction equation

HRID 874191 reaction equation
[C:1]([C:4]1[CH:5]=[C:6]([C:16]([O:18][CH3:19])=[O:17])[N:7]([C:9]2[C:14]([Cl:15])=[CH:13][CH:12]=[CH:11][N:10]=2)[CH:8]=1)(=[O:3])[CH3:2].[Br:20]Br>O1CCOCC1>[Br:20][CH2:2][C:1]([C:4]1[CH:5]=[C:6]([C:16]([O:18][CH3:19])=[O:17])[N:7]([C:9]2[C:14]([Cl:15])=[CH:13][CH:12]=[CH:11][N:10]=2)[CH:8]=1)=[O:3]

Participants

4

Reactant 2

HCID 24408BromineHCID 67125231methyl 4-acetyl-1-(3-chloropyridin-2-yl)-1H-pyrrole-2-carboxylate

Product 1

HCID 86660452methyl 4-(bromoacetyl)-1-(3-chloropyridin-2-yl)-1H-pyrrole-2-carboxylate

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

427 mg (1.48 mmol) of methyl 4-acetyl-1-(3-chloropyridin-2-yl)-1H-pyrrole-2-carboxylate were initially charged in 12 ml of dioxane, and 284 mg (1.78 mmol) of bromine were added dropwise at RT. The mixture was then stirred under reflux for 7 h. The solvent was distilled off under reduced pressure, giving an oil which was directly, without purification, reacted further.

Workup

  1. temperatureunder reflux for 7 h
  2. distillationThe solvent was distilled off under reduced pressure
  3. customgiving an oil which
  4. customwas directly, without purification
  5. customreacted further

Sources & evidence

ORD record
ord-c95ce67d685e4b6d869e1b3c2ee20cd8
Source dataset
uspto-grants-2015_03
Patent number
US08980886B2

Reaction notes

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