Water → HCID 86698138, compound

HRID 705027Notes

Reaction equation

HRID 705027 reaction equation
CC(C)([O-])C.[K+].[CH3:7][C:8]([C:10]1[CH:15]=[CH:14][CH:13]=[N:12][CH:11]=1)=[O:9].[Br:16][C:17]1[N:22]=[C:21]([C:23](OCC)=[O:24])[CH:20]=[CH:19][CH:18]=1.O>O1CCCC1.C(O)(=O)C>[Br:16][C:17]1[N:22]=[C:21]([C:23](=[O:24])[CH2:7][C:8]([C:10]2[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=2)=[O:9])[CH:20]=[CH:19][CH:18]=1

Participants

7

Reactant 4

HCID 962WaterHCID 95893-AcetylpyridineHCID 2758810Ethyl 6-BromopicolinateHCID 23665647Potassium tert-butoxide

Product 1

HCID 86698138HCID 86698138, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 8028TetrahydrofuranSolvent

Procedure

3.71 g (33.0 mmol) of potassium tert-butoxide were added to a mixture of 4.00 g (33.0 mmol) of 3-acetopyridine and 7.60 g (33.0 mmol) of ethyl 6-bromo-2-pyridinecarboxylate in 100 ml of tetrahydrofuran. The solution was stirred at room temperature until a solid mixture has formed. 100 ml of water and 10 ml of acetic acid were then added, and the aqueous phase was subsequently extracted with dichloromethane. The combined organic phases were dried over magnesium sulfate, and the solvent was then removed under reduced pressure. The residue that remained was purified chromatographically (mobile phase: cyclohexane/ethyl acetate), the solid was then washed with diethyl ether. This gave 6.91 g (69% of theory) of 1-(6-bromopyridin-2-yl)-3-(pyridin-3-yl)propane-1,3-dione.

Workup

  1. customhas formed
  2. extractionthe aqueous phase was subsequently extracted with dichloromethane
  3. dry with materialThe combined organic phases were dried over magnesium sulfate
  4. customthe solvent was then removed under reduced pressure
  5. customThe residue that remained was purified chromatographically (mobile phase: cyclohexane/ethyl acetate)
  6. washthe solid was then washed with diethyl ether

Sources & evidence

ORD record
ord-49fcb530027841c88504a47c1cbb7adb
Source dataset
uspto-grants-2015_11
Patent number
US09173396B2

Reaction notes

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