Chloroacetone → HCID 58351061, compound

HRID 1477759Notes

Reaction equation

HRID 1477759 reaction equation
Cl[CH2:2][C:3](=[O:5])[CH3:4].[Br:6][C:7]1[N:12]=[C:11]([O:13][CH3:14])[C:10]([NH:15][CH:16]=[O:17])=[CH:9][CH:8]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C.[I-].[K+]>[Br:6][C:7]1[N:12]=[C:11]([O:13][CH3:14])[C:10]([N:15]([CH2:2][C:3](=[O:5])[CH3:4])[CH:16]=[O:17])=[CH:9][CH:8]=1

Participants

6

Reactant 3

HCID 6571ChloroacetoneHCID 10796Cesium carbonateHCID 71492501N-(6-bromo-2-methoxypyridin-3-yl)formamide

Product 1

HCID 58351061HCID 58351061, compound

Reagents, catalysts & solvents 2

HCID 4875Potassium IodideCatalystHCID 6228DimethylformamideSolvent

Procedure

Chloroactone (82 mL) was added dropwise to a suspension of N-(6-bromo-2-methoxypyridin-3-yl)formamide (159.3 g), cesium carbonate (359 g) and potassium iodide (11.4 g) IN DMF (800 mL) over seven minutes. Then, the reaction solution was stirred at room temperature for one hour and 20 minutes. The reaction solution was concentrated under reduced pressure. Ethyl acetate and water were added to the resulting residue, and the organic layer was separated. The resulting organic layer was washed with brine, dried over anhydrous magnesium sulfate and then concentrated under reduced pressure to obtain 215.2 g of the title compound. The property values of the compound are as follows.

Workup

  1. concentrationThe reaction solution was concentrated under reduced pressure
  2. additionEthyl acetate and water were added to the resulting residue
  3. customthe organic layer was separated
  4. washThe resulting organic layer was washed with brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-c0a76ea932f44446a1e433524662cd89
Source dataset
uspto-grants-2016_08
Patent number
US09403815B2

Reaction notes

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