Methyl iodide → {4-[4-Cyclopropyl-2-(2-trifluoromethoxy-phenyl)-2H-pyrazol-3-ylmethoxy]-2-methyl-phenyl}-methyl-carbamic acid tert-butyl ester

HRID 2261849Notes

Reaction equation

HRID 2261849 reaction equation
[H-].[Na+].[C:3]([O:7][C:8](=[O:38])[NH:9][C:10]1[CH:15]=[CH:14][C:13]([O:16][CH2:17][C:18]2[N:19]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=3[O:32][C:33]([F:36])([F:35])[F:34])[N:20]=[CH:21][C:22]=2[CH:23]2[CH2:25][CH2:24]2)=[CH:12][C:11]=1[CH3:37])([CH3:6])([CH3:5])[CH3:4].I[CH3:40]>CN(C=O)C>[C:3]([O:7][C:8](=[O:38])[N:9]([C:10]1[CH:15]=[CH:14][C:13]([O:16][CH2:17][C:18]2[N:19]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=3[O:32][C:33]([F:36])([F:34])[F:35])[N:20]=[CH:21][C:22]=2[CH:23]2[CH2:25][CH2:24]2)=[CH:12][C:11]=1[CH3:37])[CH3:40])([CH3:6])([CH3:5])[CH3:4]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 57443358{4-[4-Cyclopropyl-2-(2-trifluoromethoxy-phenyl)-2H-pyrazol-3-ylmethoxy]-2-methyl-phenyl}-carbamic acid tert-butyl ester

Product 1

HCID 57443359{4-[4-Cyclopropyl-2-(2-trifluoromethoxy-phenyl)-2H-pyrazol-3-ylmethoxy]-2-methyl-phenyl}-methyl-carbamic acid tert-butyl esterYield 98.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (60% in mineral oil, 183 mg, 4.58 mmol) is added to a solution of {4-[4-cyclopropyl-2-(2-trifluoromethoxy-phenyl)-2H-pyrazol-3-ylmethoxy]-2-methyl-phenyl}-carbamic acid tert-butyl ester (1.92 g, 3.81 mmol) and DMF (15 mL) in an ice bath. The mixture is stirred for 30 minutes and iodomethane (0.36 mL, 5.7 mmol) is added. The bath is removed and the mixture is stirred for 1 h and quenched with a mixture if ice and ammonium chloride. The mixture is diluted with ethyl acetate and water. The organic layer is washed with brine and dried over MgSO4 to provide 1.94 g (98%) of the title compound as an oil. LC-ES/MS m/e 518.2 (M+1).

Workup

  1. customThe bath is removed
  2. stirringthe mixture is stirred for 1 h
  3. customquenched with a mixture if ice and ammonium chloride
  4. additionThe mixture is diluted with ethyl acetate and water
  5. washThe organic layer is washed with brine
  6. dry with materialdried over MgSO4

Sources & evidence

ORD record
ord-e41a7d88407f413ead31f6eac8be4a0f
Source dataset
uspto-grants-2010_12
Patent number
US07846960B2

Reaction notes

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