Methyl iodide → HCID 59679845, compound

HRID 1924099Notes

Reaction equation

HRID 1924099 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:24]=[C:25]([O:29][CH3:30])[C:26]=1[O:27][CH3:28])[C:6]([NH:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[C:15]1[O:16][C:17]2[C:18]([N:23]=1)=[N:19][CH:20]=[CH:21][CH:22]=2)=[O:7].[H-].[Na+].I[CH3:34]>CN(C=O)C>[CH3:30][O:29][C:25]1[CH:24]=[C:5]([CH:4]=[C:3]([O:2][CH3:1])[C:26]=1[O:27][CH3:28])[C:6]([N:8]([CH3:34])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[C:15]1[O:16][C:17]2[C:18]([N:23]=1)=[N:19][CH:20]=[CH:21][CH:22]=2)=[O:7]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 59680020HCID 59680020, compound

Product 1

HCID 59679845HCID 59679845, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a suspension of 3,4,5-trimethoxy-N-(2-oxazolo[4,5-b]pyridin-2-yl-phenyl)-benzamide (0.03 g, 0.1 mmol) in 3 mL of DMF was added sodium hydride (60% dispersion in mineral oil, 0.006 g, 0.2 mmol). The mixture was stirred at RT for 30 minutes, becoming homogeneous. To this was then added iodomethane, drop wise (0.040 g, 0.3 mmol, 0.02 mL). After an additional hour at RT, the reaction was quenched with water and then partitioned between saturated NH4Cl and EtOAc. The organic layer was washed with brine and dried over MgSO4. The crude product was purified by silica chromatography, 0-5% methanol/dichloromethane. The desired product was isolated as a yellow solid. (Calc'd for C23H21N3O5: 419.44, [M+H]+ found: 420.1).

Workup

  1. waitAfter an additional hour at RT
  2. customthe reaction was quenched with water
  3. custompartitioned between saturated NH4Cl and EtOAc
  4. washThe organic layer was washed with brine
  5. dry with materialdried over MgSO4
  6. customThe crude product was purified by silica chromatography, 0-5% methanol/dichloromethane

Sources & evidence

ORD record
ord-b5859ae83e2c48279848aca76b06bb7d
Source dataset
uspto-grants-2012_05
Patent number
US08178536B2

Reaction notes

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