Methyl iodide → HCID 66980511, compound

HRID 1844510Notes

Reaction equation

HRID 1844510 reaction equation
[H-].[Na+].[N+:3]([C:6]1[CH:7]=[CH:8][C:9]([O:12][C:13]2[CH:18]=[CH:17][C:16]([NH:19][C:20](=[O:26])[O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[CH:15][CH:14]=2)=[N:10][CH:11]=1)([O-:5])=[O:4].I[CH3:28]>C1COCC1>[CH3:28][N:19]([C:16]1[CH:17]=[CH:18][C:13]([O:12][C:9]2[CH:8]=[CH:7][C:6]([N+:3]([O-:5])=[O:4])=[CH:11][N:10]=2)=[CH:14][CH:15]=1)[C:20](=[O:26])[O:21][C:22]([CH3:23])([CH3:25])[CH3:24]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 57511328HCID 57511328, compound

Product 1

HCID 66980511HCID 66980511, compoundYield 77.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a THF (30 mL) suspension of NaH (60% in oil, 1.22 g) was added tert-butyl {4-[(5-nitropyridin-2-yl)oxy]phenyl}carbamate (7.77 g) at 0° C. After stirring at 0° C. for 10 min, iodomethane (4.33 g) was added and the mixture was stirred at room temperature for 3 hours. The mixture was poured into ice water and extracted with AcOEt. The organic layer was washed with water, saturated aqueous NaCl and dried over anhydrous Na2SO4. The solvent was removed under reduced pressure. The residue was purified by silica gel column chromatography (n-hexane/AcOEt=2/1) to afford the title compound (6.30 g) as a pale yellow solid.

Workup

  1. stirringthe mixture was stirred at room temperature for 3 hours
  2. extractionextracted with AcOEt
  3. washThe organic layer was washed with water, saturated aqueous NaCl
  4. dry with materialdried over anhydrous Na2SO4
  5. customThe solvent was removed under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (n-hexane/AcOEt=2/1)

Sources & evidence

ORD record
ord-8a0d0d69bf0a480882f3eba6e1148001
Source dataset
uspto-grants-2015_02
Patent number
US08946437B2

Reaction notes

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