2-Amino-5-bromopyridine → HCID 23158249, compound

HRID 601692Notes

Reaction equation

HRID 601692 reaction equation
Cl[CH2:2][CH2:3][C:4](=O)[CH2:5][C:6]([O:8][CH2:9][CH3:10])=[O:7].[NH2:12][C:13]1[CH:18]=[CH:17][C:16]([Br:19])=[CH:15][N:14]=1>C(O)C>[Br:19][C:16]1[CH:17]=[CH:18][C:13]2[N:14]([CH:2]=[C:3]([CH2:4][CH2:5][C:6]([O:8][CH2:9][CH3:10])=[O:7])[N:12]=2)[CH:15]=1

Participants

4

Reactant 2

HCID 706222-Amino-5-bromopyridineHCID 23158165Ethyl 5-chloro-3-oxopentanoate

Product 1

HCID 23158249HCID 23158249, compoundYield 13,903.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

4.28 mg of ethyl 5-chloro-3-oxopentanoate was dissolved in 40 ml of ethanol, 2.94 g of 2-amino-5-bromopyridine was added and the mixture was stirred all night by heating under reflux. The mixture was cooled down to room temperature, and the solvents were distilled outunder reduced pressure. Ethyl acetate followed by saturated sodium bicarbonate aqueous solution were added. Organic layer was dried with anhydrous sodium sulfate, and the solvents were distilled outunder reduced pressure. The obtained residues were purified by preparative thin-layer silicagel chromatography (hexane:ethyl acetate=50:50) to obtain 990 mg of the above compound as crude product.

Workup

  1. temperatureby heating
  2. temperatureunder reflux
  3. distillationthe solvents were distilled outunder reduced pressure
  4. additionwere added
  5. dry with materialOrganic layer was dried with anhydrous sodium sulfate
  6. distillationthe solvents were distilled outunder reduced pressure
  7. customThe obtained residues were purified by preparative thin-layer silicagel chromatography (hexane:ethyl acetate=50:50)

Sources & evidence

ORD record
ord-3a4e54da656f4d77a75691cfecfd2013
Source dataset
uspto-grants-2011_03
Patent number
US07902369B2

Reaction notes

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