Methyl iodide → HCID 22388359, compound

HRID 1072923Notes

Reaction equation

HRID 1072923 reaction equation
[C:1]([NH:9][C:10]1[CH:30]=[CH:29][C:13]([CH2:14][N:15]2[C:19]3=[N:20][C:21]([C:24]([O:26][CH3:27])=[O:25])=[CH:22][CH:23]=[C:18]3[N:17]=[C:16]2[CH3:28])=[C:12]([Cl:31])[CH:11]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[CH3:34]I>CN(C)C=O>[C:1]([N:9]([C:10]1[CH:30]=[CH:29][C:13]([CH2:14][N:15]2[C:19]3=[N:20][C:21]([C:24]([O:26][CH3:27])=[O:25])=[CH:22][CH:23]=[C:18]3[N:17]=[C:16]2[CH3:28])=[C:12]([Cl:31])[CH:11]=1)[CH3:34])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 22388419HCID 22388419, compound

Product 1

HCID 22388359HCID 22388359, compoundYield 98.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of methyl 3-(4-(N-benzoylamino)-2-chlorobenzyl)-2-methyl-3H-imidazo[4,5-b]pyridine-5-carboxylate (300 mg) in N,N-dimethylformamide (3 ml) was added 60% sodium hydride (in mineral oil, 30.4 mg) at room temperature. After 15 min, methyl iodide (108 mg) was added and the mixture was stirred at room temperature for 2 hr. Ice water was poured thereinto and the mixture was extracted with ethyl acetate. The organic layer was successively washed with a saturated aqueous solution of sodium hydrogencarbonate and saturated brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure to give the objective compound (305 mg) as a pale-yellow powder.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was successively washed with a saturated aqueous solution of sodium hydrogencarbonate and saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-75708897e599478495c58ac11e9e5de0
Source dataset
uspto-grants-2005_06
Patent number
US06911469B2

Reaction notes

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