Methyl iodide → HCID 57683055, compound

HRID 494319Notes

Reaction equation

HRID 494319 reaction equation
[CH3:1][O:2][C:3]([C:5]1[NH:6][CH:7]=[C:8]([C:10]([C:12]2[C:13]([C:18]3[CH:23]=[CH:22][C:21]([Br:24])=[CH:20][CH:19]=3)=[N:14][O:15][C:16]=2[CH3:17])=[O:11])[CH:9]=1)=[O:4].[H-].[Na+].I[CH3:28]>O>[CH3:1][O:2][C:3]([C:5]1[N:6]([CH3:28])[CH:7]=[C:8]([C:10]([C:12]2[C:13]([C:18]3[CH:19]=[CH:20][C:21]([Br:24])=[CH:22][CH:23]=3)=[N:14][O:15][C:16]=2[CH3:17])=[O:11])[CH:9]=1)=[O:4]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 57682992HCID 57682992, compound2×

Product 1

HCID 57683055HCID 57683055, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 212 mg (0.5 mmol) 4-[3-(4-bromo-phenyl)-5-methyl-isoxazole-4-carbonyl]-1H-pyrrole-2-carboxylic acid methyl ester (intermediate 2, step 2), 28 mg (0.66 mmol) NaH and 116 mg (0.65 mmol) iodomethane was stirred at room temperature for 24 h. The mixture was then diluted with water and the product extracted with ethyl acetate. The combined organic extracts were then dried with Na2SO4 and evaporated to yield 133 mg (61%) of the title compound as a light yellow solid after purification by chromatography on silica gel eluting with ethyl acetate/heptane. (m/e): 403.3/405.2 (M+H, 100%).

Workup

  1. extractionthe product extracted with ethyl acetate
  2. dry with materialThe combined organic extracts were then dried with Na2SO4
  3. customevaporated

Sources & evidence

ORD record
ord-185aef324b294f869c773b53c37460e2
Source dataset
uspto-grants-2009_05
Patent number
US07538132B2

Reaction notes

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