Methyl iodide → HCID 58188125, compound

HRID 1845292Notes

Reaction equation

HRID 1845292 reaction equation
[OH:1][CH2:2][C:3]1[CH:4]=[C:5]([CH:10]=[C:11]([C:13]2[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][N:14]=2)[CH:12]=1)[C:6]([O:8][CH3:9])=[O:7].[H-].[Na+].[CH3:22]I>CN(C)C=O>[CH3:22][O:1][CH2:2][C:3]1[CH:4]=[C:5]([CH:10]=[C:11]([C:13]2[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][N:14]=2)[CH:12]=1)[C:6]([O:8][CH3:9])=[O:7]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 58188278HCID 58188278, compound

Product 1

HCID 58188125HCID 58188125, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of methyl 3-(hydroxymethyl)-5-(5-methylpyridin-2-yl)benzoate (110 mg, 0.41 mmol) in N,N-dimethylformamide (2 mL) at 0° C. was added sodium hydride (60% in mineral oil, 21 mg, 0.52 mmol). After 30 minutes, methyl iodide (73 mg, 0.51 mmol) was added at 0° C. The mixture was warmed to room temperature and stirred for 30 minutes. The mixture was quenched with water (2 mL) and extracted with EtOAc. The combined organic layers were dried over anhydrous MgSO4 and concentrated to get the tittle compound.

Workup

  1. customThe mixture was quenched with water (2 mL)
  2. extractionextracted with EtOAc
  3. dry with materialThe combined organic layers were dried over anhydrous MgSO4
  4. concentrationconcentrated
  5. customto get the tittle compound

Sources & evidence

ORD record
ord-ecd787d925db4203881ebe69df16aab1
Source dataset
uspto-grants-2015_02
Patent number
US08946439B2

Reaction notes

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