Hydrochloric Acid → Cyclohexyl(3-methylfuro[3,2-b]pyridin-2-yl)methanone

HRID 2091207Notes

Reaction equation

HRID 2091207 reaction equation
[OH:1][C:2]1[C:3]([C:8](=O)[CH3:9])=[N:4][CH:5]=[CH:6][CH:7]=1.Br[CH2:12][C:13]([CH:15]1[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1)=[O:14].C(=O)([O-])[O-].[K+].[K+].Cl>CN(C)C=O>[CH:15]1([C:13]([C:12]2[O:1][C:2]3[C:3](=[N:4][CH:5]=[CH:6][CH:7]=3)[C:8]=2[CH3:9])=[O:14])[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 111600272-Bromo-1-cyclohexylethanoneHCID 140889471-(3-Hydroxypyridin-2-yl)ethan-1-one

Product 1

HCID 66777549Cyclohexyl(3-methylfuro[3,2-b]pyridin-2-yl)methanoneYield 53%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of 1-(3-hydroxypyridin-2-yl)ethanone (4.37 g), 2-bromo-1-cyclohexylethanone (9.82 g) synthesized in Example A51(1) and N,N-dimethylformamide (50 mL) was added potassium carbonate (13.2 g), and the mixture was stirred at room temperature for 2.5 days. 1N Hydrochloric acid 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 purified by silica gel column chromatography (20% ethyl acetate/hexane) to give the title object compound (4.09 g, 53%) as a brown 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. customThe residue was purified by silica gel column chromatography (20% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-6c074e6de8944d27b331aba49216e674
Source dataset
uspto-grants-2013_05
Patent number
US08436043B2

Reaction notes

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