Methyl iodide → HCID 86719573, compound

HRID 2208907Notes

Reaction equation

HRID 2208907 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:13][CH2:14][CH:15]2[CH2:20][CH2:19][O:18][CH2:17][CH2:16]2)[C:5]([CH3:12])=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8].[C:21](=O)([O-])[O-].[Cs+].[Cs+].CI>C(#N)C>[Cl:1][C:2]1[CH:3]=[C:4]([N:13]([CH3:21])[CH2:14][CH:15]2[CH2:20][CH2:19][O:18][CH2:17][CH2:16]2)[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 70873982HCID 70873982, compound

Product 1

HCID 86719573HCID 86719573, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

To a stirred solution of methyl 5-chloro-2-methyl-3-(((tetrahydro-2H-pyran-4-yl)methyl)amino)benzoate (0.80 g, 2.71 mmol) in acetonitrile (20 mL), cesium carbonate (1.75 g, 5.42 mmol) and methyl iodide (1.93 g, 13.6 mmol) were added. The resulting reaction mass was heated at 80° C. for 8 h. On completion, the mixture was cooled to room temperature and filtered. The residue was washed with ethyl acetate and the filtrate was concentrated to give crude material which was purified by column chromatography to give the title compound (0.70 g, 84%).

Workup

  1. customThe resulting reaction mass
  2. temperatureOn completion, the mixture was cooled to room temperature
  3. filtrationfiltered
  4. washThe residue was washed with ethyl acetate
  5. concentrationthe filtrate was concentrated
  6. customto give crude material which
  7. customwas purified by column chromatography

Sources & evidence

ORD record
ord-eb9c5a5c6cac4f7dbd90c3026f7fdbef
Source dataset
uspto-grants-2016_06
Patent number
US09376422B2

Reaction notes

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