Potassium Carbonate → (5-Bromo-3-methylfuro[3,2-b]pyridin-2-yl)(cyclohexyl)methanone

HRID 2091250

Reaction equation

HRID 2091250 reaction equation
[Br:1][C:2]1[N:7]=[C:6]([C:8](=O)[CH3:9])[C:5]([OH:11])=[CH:4][CH:3]=1.Br[CH2:13][C:14]([CH:16]1[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1)=[O:15].C(=O)([O-])[O-].[K+].[K+].[Cl-].[NH4+]>CN(C)C=O>[Br:1][C:2]1[N:7]=[C:6]2[C:8]([CH3:9])=[C:13]([C:14]([CH:16]3[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]3)=[O:15])[O:11][C:5]2=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 25517Ammonium ChlorideHCID 111600272-Bromo-1-cyclohexylethanoneHCID 722180151-(6-Bromo-3-hydroxypyridin-2-YL)ethanone

Product 1

HCID 86662737(5-Bromo-3-methylfuro[3,2-b]pyridin-2-yl)(cyclohexyl)methanoneYield 35.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of 1-(6-bromo-3-hydroxypyridin-2-yl)ethanone (1.64 g) synthesized above, 2-bromo-1-cyclohexylethanone (2.34 g) synthesized in Example A51(1) and N,N-dimethylformamide (20 mL) was added potassium carbonate (3.15 g), and the mixture was stirred overnight at room temperature. Saturated aqueous ammonium chloride solution was added to quench the reaction, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure. The residue was washed with diisopropyl ether to give the title object compound (865 mg, 35%) as a white solid.

Workup

  1. customto quench
  2. customthe reaction
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe extract was washed with saturated brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. washThe residue was washed with diisopropyl ether

Sources & evidence

ORD record
ord-72676036e1424762945985dca6dc9069
Source dataset
uspto-grants-2013_05
Patent number
US08436043B2

Linked notes

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