Methyl iodide → HCID 59749682, compound

HRID 747480Notes

Reaction equation

HRID 747480 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6](=[O:16])[CH2:7][C:8]1[CH:9]=[N:10][C:11]([O:14]C)=[CH:12][CH:13]=1.I[CH3:18]>CC(OC)(C)C>[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6](=[O:16])[CH2:7][C:8]1[CH:13]=[CH:12][C:11](=[O:14])[N:10]([CH3:18])[CH:9]=1

Participants

4

Reactant 2

HCID 6328Methyl iodideHCID 59749685HCID 59749685, compound

Product 1

HCID 59749682HCID 59749682, compoundYield 287.1%

Reagents, catalysts & solvents 1

HCID 15413tert-Butyl methyl etherSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 1-furan-2-yl-2-(6-methoxy-pyridin-3-yl)-ethanone (7) (800.0 g, content 625.6 g, 2.88 mol) obtained in Preparation Example 4 in N-methyl-2-pyrrolidine (NMP) (1.88 L) was added iodomethane (122.6 g, 0.86 mol), and the reaction mixture was stirred at 100° C. for 3 hours and then at room temperature for 17.5 hours. To the reaction mixture was added dropwise MTBE (6.6 L) over a period of 77 minutes, followed by stirring for 1 hour while cooling in an ice bath. The precipitated crystals were collected by filtration and washed with MTBE (2.0 L), and then dried under reduced pressure at 50° C. for 3 hours to give 692.0 g of a crude product of the title compound as a dark brown powder (content 536.4 g, yield 85.7%).

Workup

  1. waitat room temperature for 17.5 hours
  2. stirringby stirring for 1 hour
  3. temperaturewhile cooling in an ice bath
  4. filtrationThe precipitated crystals were collected by filtration
  5. washwashed with MTBE (2.0 L)
  6. customdried under reduced pressure at 50° C. for 3 hours

Sources & evidence

ORD record
ord-19028ab715364253966eec2a9231b7ad
Source dataset
uspto-grants-2008_07
Patent number
US07396928B2

Reaction notes

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