Methyl iodide → HCID 67215234, compound

HRID 1983153Notes

Reaction equation

HRID 1983153 reaction equation
[CH3:1][C:2]1[O:6][N:5]=[C:4]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[C:3]=1[C:13]1[O:17][C:16]([C:18]2[CH:19]=[C:20]3[C:24](=[CH:25][CH:26]=2)[NH:23][CH:22]=[CH:21]3)=[N:15][N:14]=1.[C:27](=O)([O-])[O-].[K+].[K+].IC>CN(C=O)C>[CH3:27][N:23]1[C:24]2[C:20](=[CH:19][C:18]([C:16]3[O:17][C:13]([C:3]4[C:4]([C:7]5[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=5)=[N:5][O:6][C:2]=4[CH3:1])=[N:14][N:15]=3)=[CH:26][CH:25]=2)[CH:21]=[CH:22]1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 67215437HCID 67215437, compound

Product 1

HCID 67215234HCID 67215234, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 5-[5-(5-methyl-3-phenyl-isoxazol-4-yl)-[1,3,4]oxadiazol-2-yl]-1H-indole (150 mg, 0.44 mmol) in DMF (2 mL) was added potassium carbonate (121 mg, 0.88 mmol) and iodomethane (0.04 ml, 0.66 mmol) and the reaction mixture was stirred for 3 d in a closed round bottomed flask at ambient temperature. The mixture was extracted with water (20 ml) and ethyl acetate (20 mL). The aqueous layer was extracted with ethyl acetate and the combined organic layers were washed with aqueous sodium carbonate (half saturated, 20 mL) and brine (20 mL). Drying over sodium sulfate and purification by chromatography (SiO2, heptane:ethyl acetate:dichloromethane=70:10:20 to 40:40:20) afforded the title compound (136 mg, 87%) as a white solid. MS: m/e=357.2 [M+H]+.

Workup

  1. extractionThe mixture was extracted with water (20 ml) and ethyl acetate (20 mL)
  2. extractionThe aqueous layer was extracted with ethyl acetate
  3. washthe combined organic layers were washed with aqueous sodium carbonate (half saturated, 20 mL) and brine (20 mL)
  4. dry with materialDrying over sodium sulfate and purification by chromatography (SiO2, heptane:ethyl acetate:dichloromethane=70:10:20 to 40:40:20)

Sources & evidence

ORD record
ord-76e02b3c10ea4c83b88c84caa7cfbdfe
Source dataset
uspto-grants-2009_06
Patent number
US07541372B2

Reaction notes

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