Trimethylsilyl iodide → 3-[(1S)-2-Hydroxy-1-methylethoxy]-N-(1-methyl-1H-pyrazol-3-yl)-5-[4-(1,2,4-oxadiazol-3-yl)phenoxy]benzamide

HRID 20555Notes

Reaction equation

HRID 20555 reaction equation
C[Si](I)(C)C.C[O:7][CH2:8][C@H:9]([CH3:38])[O:10][C:11]1[CH:12]=[C:13]([CH:23]=[C:24]([O:26][C:27]2[CH:32]=[CH:31][C:30]([C:33]3[N:37]=[CH:36][O:35][N:34]=3)=[CH:29][CH:28]=2)[CH:25]=1)[C:14]([NH:16][C:17]1[CH:21]=[CH:20][N:19]([CH3:22])[N:18]=1)=[O:15]>C(#N)C.C(OCC)(=O)C>[OH:7][CH2:8][C@H:9]([CH3:38])[O:10][C:11]1[CH:12]=[C:13]([CH:23]=[C:24]([O:26][C:27]2[CH:32]=[CH:31][C:30]([C:33]3[N:37]=[CH:36][O:35][N:34]=3)=[CH:29][CH:28]=2)[CH:25]=1)[C:14]([NH:16][C:17]1[CH:21]=[CH:20][N:19]([CH3:22])[N:18]=1)=[O:15]

Participants

5

Reactant 2

HCID 85247Trimethylsilyl iodideHCID 115180333-[(1S)-2-methoxy-1-methylethoxy]-N-(1-methyl-1H-pyrazol-3-yl)-5-[4-(1,2,4-oxadiazol-3-yl)phenoxy]benzamide

Product 1

HCID 115248923-[(1S)-2-Hydroxy-1-methylethoxy]-N-(1-methyl-1H-pyrazol-3-yl)-5-[4-(1,2,4-oxadiazol-3-yl)phenoxy]benzamideYield 84.5%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

Trimethylsilyl iodide (0.062 mL, 0.434 mmol) was added to a solution of 3-[(1S)-2-methoxy-1-methylethoxy]-N-(1-methyl-1H-pyrazol-3-yl)-5-[4-(1,2,4-oxadiazol-3-yl)phenoxy]benzamide (78 mg, 0.174 mmol) in acetonitrile (2 mL) and the reaction mixture allowed to stir at RT for 18 hours. The reaction was diluted with ethyl acetate (15 mL) and quenched by the addition of saturated aqueous sodium bicarbonate (20 mL). The organic phase was washed with saturated aqueous thiosulphate solution (20 mL) and dried (MgSO4). The volatiles were removed under reduced pressure and the resulting oil purified by chromatography on silica, eluting with 0-100% ethyl acetate in iso-hexane, to give the title compound as a colourless solid (64 mg).

Workup

  1. customquenched by the addition of saturated aqueous sodium bicarbonate (20 mL)
  2. washThe organic phase was washed with saturated aqueous thiosulphate solution (20 mL)
  3. dry with materialdried (MgSO4)
  4. customThe volatiles were removed under reduced pressure
  5. customthe resulting oil purified by chromatography on silica
  6. washeluting with 0-100% ethyl acetate in iso-hexane

Sources & evidence

ORD record
ord-e5ba994d89af467e91beaf16cefaea5f
Source dataset
uspto-grants-2010_06
Patent number
US07745475B2

Reaction notes

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