Methyl iodide → HCID 131724447, compound

HRID 352139Notes

Reaction equation

HRID 352139 reaction equation
[CH3:1][C:2]([O:5][C:6](=[O:28])[NH:7][CH2:8][CH2:9][CH2:10][C@@H:11]([O:17][C:18]1[CH:23]=[C:22]([Cl:24])[C:21]([F:25])=[CH:20][C:19]=1[C:26]#[N:27])[C:12]1[CH:16]=[CH:15][O:14][CH:13]=1)([CH3:4])[CH3:3].[H-].[Na+].[CH3:31]I.[Cl-].[NH4+]>O1CCCC1>[CH3:4][C:2]([O:5][C:6](=[O:28])[N:7]([CH2:8][CH2:9][CH2:10][C@@H:11]([O:17][C:18]1[CH:23]=[C:22]([Cl:24])[C:21]([F:25])=[CH:20][C:19]=1[C:26]#[N:27])[C:12]1[CH:16]=[CH:15][O:14][CH:13]=1)[CH3:31])([CH3:1])[CH3:3]

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 131724448HCID 131724448, compound

Product 1

HCID 131724447HCID 131724447, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The product of Example 41 step (c) (0.68 g) was dissolved in dry tetrahydrofuran (40 ml) and treated with sodium hydride (60% dispersion in oil, 0.3 g) and stirred under nitrogen for 0.5 h. Methyl iodide (3 ml) was added and the reaction mixture stirred at ambient temperature for 48 h. The mixture was then cooled in an ice-bath and carefully treated with saturated ammonium chloride (50 ml) and extracted into ethyl acetate. The organic extract was washed with water, brine, dried over magnesium sulphate and evaporated to give a yellow oil (0.7 g).

Workup

  1. stirringthe reaction mixture stirred at ambient temperature for 48 h
  2. temperatureThe mixture was then cooled in an ice-bath
  3. extractionextracted into ethyl acetate
  4. extractionThe organic extract
  5. washwas washed with water, brine
  6. dry with materialdried over magnesium sulphate
  7. customevaporated

Sources & evidence

ORD record
ord-5389aff657554c8cb661abb1c37bd128
Source dataset
uspto-grants-2004_06
Patent number
US06743939B2

Reaction notes

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