Methyl iodide → HCID 70872667, compound

HRID 2208713Notes

Reaction equation

HRID 2208713 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, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of methyl 5-bromo-3-(cyclopentylamino)-2-methylbenzoate (1 g, 3.22 mmol), Cs2CO3 (2.10 g, 6.45 mmol) and methyl iodide (2.3 g, 16.12 mmol) in acetonitrile (15 mL) was heated at 80° C. for 14 h. After complete consumption of starting material reaction mixture was filtered. The filtrate was concentrated and the obtained residue was purified by column chromatography to provide the desired compound (0.9 g, 86%).

Workup

  1. customAfter complete consumption of starting material reaction mixture
  2. filtrationwas filtered
  3. concentrationThe filtrate was concentrated
  4. customthe obtained residue was purified by column chromatography

Sources & evidence

ORD record
ord-252ca05abbfe4137ab451edcda325ba1
Source dataset
uspto-grants-2016_06
Patent number
US09376422B2

Reaction notes

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