Methyl iodide → HCID 53745957, compound

HRID 1597372Notes

Reaction equation

HRID 1597372 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. temperatureagain 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-5737f287d43b4ac8832c6f7556ceca82
Source dataset
uspto-grants-2001_09
Patent number
US06294566B1

Reaction notes

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