Methyl iodide → HCID 70874079, compound

HRID 2208739Notes

Reaction equation

HRID 2208739 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([NH:13][CH:14]2[CH2:19][CH2:18][N:17]([CH3:20])[CH2:16][CH2:15]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>[Br:1][C:2]1[CH:3]=[C:4]([N:13]([CH3:21])[CH:14]2[CH2:19][CH2:18][N:17]([CH3:20])[CH2:16][CH2:15]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 70874041HCID 70874041, compound

Product 1

HCID 70874079HCID 70874079, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

To a stirred solution of methyl 5-bromo-2-methyl-3-((1-methylpiperidin-4-yl)amino)benzoate (0.6 g, 1.76 mmol) in acetonitrile (15 mL), cesium carbonate (1.14 g, 3.52 mmol) and methyl iodide (1.2 g, 8.8 mmol) were added; resulting reaction mass was heated at 80° C. for 7 h. On completion, reaction mass was cooled to room temperature and filtered, residue was washed with ethyl acetate and filtrate was concentrated and then purified by column chromatography to afford the desired compound (0.5 g, 80%).

Workup

  1. customresulting
  2. customreaction mass
  3. customOn completion, reaction mass
  4. temperaturewas cooled to room temperature
  5. filtrationfiltered
  6. washresidue was washed with ethyl acetate and filtrate
  7. concentrationwas concentrated
  8. custompurified by column chromatography

Sources & evidence

ORD record
ord-b36394c6503f420aab5324c51ed0c855
Source dataset
uspto-grants-2016_06
Patent number
US09376422B2

Reaction notes

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