Methyl iodide → HCID 70873764, compound

HRID 2208741Notes

Reaction equation

HRID 2208741 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([NH:13][CH:14]([CH3:16])[CH3:15])[C:5]([CH3:12])=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8].[C:17]([O-])([O-])=O.[Cs+].[Cs+].CI>C(#N)C>[Br:1][C:2]1[CH:3]=[C:4]([N:13]([CH:14]([CH3:16])[CH3:15])[CH3:17])[C:5]([CH3:12])=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 10796Cesium carbonateHCID 70874071HCID 70874071, compound

Product 1

HCID 70873764HCID 70873764, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

To a stirred solution of methyl 5-bromo-3-(isopropylamino)-2-methylbenzoate (0.5 g, 1.75 mmol) in acetonitrile (10 mL), Cs2CO3 (1.02 g, 2.63 mmol) and methyl iodide (1.45 g, 3.5 mmol) were added to it. The resulting reaction mixture was stirred at 80° C. for 4 h. Upon completion, the solvent was removed under reduced pressure and residue dissolved in water and extracted with ethyl acetate. Crude material obtained was purified by column chromatography over silica gel affording the desired compound product without further purification (0.39 g)

Workup

  1. customThe resulting reaction mixture
  2. customUpon completion, the solvent was removed under reduced pressure and residue
  3. dissolutiondissolved in water
  4. extractionextracted with ethyl acetate
  5. customCrude material obtained
  6. customwas purified by column chromatography over silica gel affording the desired compound product
  7. customwithout further purification (0.39 g)

Sources & evidence

ORD record
ord-4332d3081def4e24bc021732a2d5d72b
Source dataset
uspto-grants-2016_06
Patent number
US09376422B2

Reaction notes

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