Methyl iodide → HCID 70872667, compound

HRID 2208679Notes

Reaction equation

HRID 2208679 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([NH:13][CH:14]2[CH2:18][CH2:17][CH2:16][CH2:15]2)[C:5]([CH3:12])=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8].[C:19]([O-])([O-])=O.[Cs+].[Cs+].CI>C(#N)C>[Br:1][C:2]1[CH:3]=[C:4]([N:13]([CH:14]2[CH2:18][CH2:17][CH2:16][CH2:15]2)[CH3:19])[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 70872494HCID 70872494, compound

Product 1

HCID 70872667HCID 70872667, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

To a stirred solution of methyl 5-bromo-3-(cyclopentylamino)-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-9d1ce0cd267c44ce83dcae84c008ecfd
Source dataset
uspto-grants-2016_06
Patent number
US09376422B2

Reaction notes

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