Methyl iodide → HCID 53745957, compound

HRID 1836303Notes

Reaction equation

HRID 1836303 reaction equation
[CH3:1]CCCC.[H-].[Na+].[CH3:8][N:9]([CH3:37])[S:10]([N:13]1[CH:17]=[C:16]([CH:18]([OH:29])[C:19]2[C:28]3[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=3)[N:22]=[CH:21][CH:20]=2)[N:15]=[C:14]1[Si:30]([C:33]([CH3:36])([CH3:35])[CH3:34])([CH3:32])[CH3:31])(=[O:12])=[O:11].CI>C1COCC1>[CH3:8][N:9]([CH3:37])[S:10]([N:13]1[CH:17]=[C:16]([CH:18]([O:29][CH3:1])[C:19]2[C:28]3[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=3)[N:22]=[CH:21][CH:20]=2)[N:15]=[C:14]1[Si:30]([C:33]([CH3:34])([CH3:36])[CH3:35])([CH3:32])[CH3:31])(=[O:11])=[O:12]

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 8003PentaneHCID 24758Sodium hydrideHCID 54026974HCID 54026974, compound

Product 1

HCID 53745957HCID 53745957, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To pentane washed sodium hydride (0.048 g, 1.2 mmol) in 5 ml of THF at 0° C., 2-(tert-Butyldimethylsilyl)-4-(hydroxyquinolin-4-yl-methyl)-imidazole-1-sulfonic acid dimethylamide (example 8, step A) (0.375 g, 0.811 mmol) was added slowly over a period of 5 minutes. After stirring at room temperature for 15 minutes, it was again cooled to 0° C. and methyl iodide (0.1 ml, 1.62 mmol) was added neat. The reaction mixture was stirred at room temperature for 1 hour, concentrated under reduced pressure and partitioned between EtOAc (10 ml) and water (10 ml). The organic layer was dried over sodium sulfate, filtered and concentrated to yield 0.32 g (83%) of the product as a syrup.

Workup

  1. temperatureit was again cooled to 0° C.
  2. stirringThe reaction mixture was stirred at room temperature for 1 hour
  3. concentrationconcentrated under reduced pressure
  4. custompartitioned between EtOAc (10 ml) and water (10 ml)
  5. dry with materialThe organic layer was dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-7cdf107bfe374a5f9a1572be84f6b94f
Source dataset
uspto-grants-2004_08
Patent number
US06777426B2

Reaction notes

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