Methyl iodide → HCID 67528435, compound

HRID 2261748Notes

Reaction equation

HRID 2261748 reaction equation
[C:1]([O:5][C:6](=[O:33])[NH:7][C:8]1[CH:13]=[CH:12][C:11]([O:14][CH2:15][C:16]2[N:17]([C:24]3[C:29]([Cl:30])=[CH:28][CH:27]=[CH:26][C:25]=3[Cl:31])[N:18]=[CH:19][C:20]=2[CH:21]([CH3:23])[CH3:22])=[CH:10][C:9]=1[CH3:32])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].I[CH3:37]>CN(C=O)C>[C:1]([O:5][C:6](=[O:33])[N:7]([C:8]1[CH:13]=[CH:12][C:11]([O:14][CH2:15][C:16]2[N:17]([C:24]3[C:29]([Cl:30])=[CH:28][CH:27]=[CH:26][C:25]=3[Cl:31])[N:18]=[CH:19][C:20]=2[CH:21]([CH3:23])[CH3:22])=[CH:10][C:9]=1[CH3:32])[CH3:37])([CH3:2])([CH3:3])[CH3:4]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 67528028HCID 67528028, compound

Product 1

HCID 67528435HCID 67528435, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

To a 0° C. solution of {4-[2-(2,6-dichloro-phenyl)-4-isopropyl-2H-pyrazol-3-ylmethoxy]-2-methyl-phenyl}-carbamic acid tert-butyl ester (1.9 g, 3.9 mmol) in DMF (15 mL) is added sodium hydride (60% dispersion in mineral oil, 0.19 g, 4.7 mmol) portionwise. The mixture is stirred at 0° C. for 30 minutes. Iodomethane (0.83 g, 5.9 mmol) is added dropwise. The reaction mixture is then stirred at room temperature for 1.0 h. The reaction is quenched with the addition of saturated ammonium chloride (20 mL) at 0° C. The reaction mixture is partitioned between EtOAc (30 mL) and water (20 mL). The organic phase is washed with brine (30 mL), dried (Na2SO4), filtered, and concentrated under reduced pressure to yield the title compound (1.85 g, 95%) as a foamy solid. LC-ES/MS m/e 526.0 (M+23).

Workup

  1. stirringThe reaction mixture is then stirred at room temperature for 1.0 h
  2. customThe reaction is quenched with the addition of saturated ammonium chloride (20 mL) at 0° C
  3. customThe reaction mixture is partitioned between EtOAc (30 mL) and water (20 mL)
  4. washThe organic phase is washed with brine (30 mL)
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-3837165dd6f046449f820a0ad2aae789
Source dataset
uspto-grants-2010_12
Patent number
US07846960B2

Reaction notes

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