Methyl iodide → HCID 16722693, compound

HRID 1983097Notes

Reaction equation

HRID 1983097 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH:26][C:27]([CH:29]2[CH2:31][CH2:30]2)=[O:28])[CH:6]=[CH:7][C:8]=1[C:9]1[O:10][C:11]([C:14]2[C:15]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[N:16][O:17][C:18]=2[CH3:19])=[N:12][N:13]=1.[CH3:32][Si]([N-][Si](C)(C)C)(C)C.[K+].IC>CN(C=O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([N:26]([CH3:32])[C:27]([CH:29]2[CH2:30][CH2:31]2)=[O:28])[CH:6]=[CH:7][C:8]=1[C:9]1[O:10][C:11]([C:14]2[C:15]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[N:16][O:17][C:18]=2[CH3:19])=[N:12][N:13]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 3251421Potassium bis(trimethylsilyl)amideHCID 16722590HCID 16722590, compound

Product 1

HCID 16722693HCID 16722693, compoundYield 58.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of cyclopropanecarboxylic acid {3-methoxy-4-[5-(5-methyl-3-phenyl-isoxazol-4-yl)-[1,3,4]oxadiazol-2-yl]-phenyl}-amide (138 mg, 0.33 mmol) in DMF (2 mL) was added at ambient temperature potassium bis(trimethylsilyl)amide (0.91 M in THF, 0.44 mL, 0.40 mmol). After the dark brown solution was stirred for 15 min iodomethane (25 μL, 0.40 mmol) was added and the reaction mixture was stirred for 18 h in a closed flask. It was then extracted with water (20 mL) and ethyl acetate (20 mL). The combined organic layers were then washed with aqueous sodium carbonate (saturated, 20 mL), concentrated, dissolved in ethyl acetate (3 mL) and treated with heptane (3 mL). The resulting suspension was filtered off and washed with ethyl acetate:heptane 1:1 (3 mL) affording the title compound (83 mg, 58%) as a white solid. MS: m/e=431.3 [M+H]+.

Workup

  1. additionwas added
  2. extractionIt was then extracted with water (20 mL) and ethyl acetate (20 mL)
  3. washThe combined organic layers were then washed with aqueous sodium carbonate (saturated, 20 mL)
  4. concentrationconcentrated
  5. dissolutiondissolved in ethyl acetate (3 mL)
  6. additiontreated with heptane (3 mL)
  7. filtrationThe resulting suspension was filtered off
  8. washwashed with ethyl acetate:heptane 1:1 (3 mL)

Sources & evidence

ORD record
ord-489a1ae5f549474cb5d623df8940fd5d
Source dataset
uspto-grants-2009_06
Patent number
US07541372B2

Reaction notes

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