Potassium Iodide → HCID 58351061, compound

HRID 475719Notes

Reaction equation

HRID 475719 reaction equation
[Br:1][C:2]1[N:7]=[C:6]([O:8][CH3:9])[C:5]([NH:10][CH:11]=[O:12])=[CH:4][CH:3]=1.[I-].[K+].C(=O)([O-])[O-].[Cs+].[Cs+].Cl[CH2:22][C:23](=[O:25])[CH3:24]>CN(C=O)C>[Br:1][C:2]1[N:7]=[C:6]([O:8][CH3:9])[C:5]([N:10]([CH2:22][C:23](=[O:25])[CH3:24])[CH:11]=[O:12])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 6571ChloroacetoneHCID 10796Cesium carbonateHCID 71492501N-(6-bromo-2-methoxypyridin-3-yl)formamide

Product 1

HCID 58351061HCID 58351061, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of N-(6-bromo-2-methoxypyridin-3-yl)formamide (5.69 g, 24.63 mmol), potassium iodide (0.450 g, 2.71 mmol) and cesium carbonate (28.1 g, 86 mmol) in 66 mL of DMF was added 1-chloropropan-2-one (4.90 mL, 61.6 mmol). The reaction mixture was stirred at rt for 3 days. The reaction mixture was poured into icewater and extracted with ethyl acetate. The combined organic extracts were dried over anhydrous magnesium sulfate and filtered. The solvent was removed in vacuum to give N-(6-bromo-2-methoxypyridin-3-yl)-N-(2-oxopropyl)formamide (7.07 g, 24.62 mmol, 100% yield) as brown solid. LC-MS (M+Na)+=310.9.

Workup

  1. additionThe reaction mixture was poured into icewater
  2. extractionextracted with ethyl acetate
  3. dry with materialThe combined organic extracts were dried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. customThe solvent was removed in vacuum

Sources & evidence

ORD record
ord-75212d285d6b49569884e2ad8fda0dcc
Source dataset
uspto-grants-2014_01
Patent number
US08637525B2

Reaction notes

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