Methyl iodide → HCID 67423594, compound

HRID 1393018Notes

Reaction equation

HRID 1393018 reaction equation
[CH3:1][N:2]1[CH2:23][C:8]23[CH2:9][CH2:10][CH:11]4[CH:20]([CH:7]2[CH2:6][CH2:5][CH:4]3[CH:3]1[CH3:24])[CH2:19][CH:18]=[C:17]1[C:12]4([CH3:22])[CH2:13][CH2:14][CH:15]([OH:21])[CH2:16]1.[H-].[Na+].I[CH3:28]>CN(C=O)C>[CH3:28][O:21][CH:15]1[CH2:16][C:17]2[C:12]([CH3:22])([CH:11]3[CH:20]([CH2:19][CH:18]=2)[CH:7]2[CH2:6][CH2:5][CH:4]4[CH:3]([CH3:24])[N:2]([CH3:1])[CH2:23][C:8]24[CH2:9][CH2:10]3)[CH2:13][CH2:14]1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 67422524HCID 67422524, compound

Product 1

HCID 67423594HCID 67423594, compoundYield 38.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Compound 130A (30 mg, 0.091 mmol) was dissolved in 1.5 mL anhydrous DMF. Sodium hydride (60% dispersion in mineral oil, 6 mg, 0.137 mmol) was added and the mixture was stirred at room temperature for 1 hour before iodomethane (39 mg, 0.274 mmol) was added. The reaction mixture and stirred overnight, quenched with water and extracted with dichloromethane to give the crude product, which was purified on silica gel column eluted with 0.3% ammonium hydroxide and 5% methanol in dichloromethane to give the desired product (12 mg, 38% yield).

Workup

  1. additionwas added
  2. customquenched with water
  3. extractionextracted with dichloromethane
  4. customto give the crude product, which
  5. customwas purified on silica gel column
  6. washeluted with 0.3% ammonium hydroxide and 5% methanol in dichloromethane

Sources & evidence

ORD record
ord-254efc8dcf2d45b385b7958f9b0d1731
Source dataset
uspto-grants-2008_03
Patent number
US07345034B2

Reaction notes

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