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

HRID 2091261Notes

Reaction equation

HRID 2091261 reaction equation
[Cl: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>[Cl: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 722139671-(6-Chloro-3-hydroxypyridin-2-YL)ethan-1-one

Product 1

HCID 86662745(5-Chloro-3-methylfuro[3,2-b]pyridin-2-yl)(cyclohexyl)methanoneYield 73%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of 1-(6-chloro-3-hydroxypyridin-2-yl)ethanone (4.89 g) synthesized above, 2-bromo-1-cyclohexylethanone (7.01 g) synthesized in Example A51(1) and N,N-dimethylformamide (50 mL) was added potassium carbonate (11.8 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 (5.78 g, 73%) 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-33875e527edc446e83e6db5fa55aabbb
Source dataset
uspto-grants-2013_05
Patent number
US08436043B2

Reaction notes

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