Water → 3-(((1S)-2-Hydroxy-1-methylethyl)oxy)-N-(1-methyl-1H-pyrazol-3-yl)-5-(4-(methylsulfonyl)phenoxy)benzamide

HRID 20497

Reaction equation

HRID 20497 reaction equation
C[Si](I)(C)C.C[O:7][CH2:8][C@H:9]([CH3:37])[O:10][C:11]1[CH:12]=[C:13]([CH:23]=[C:24]([O:26][C:27]2[CH:32]=[CH:31][C:30]([S:33]([CH3:36])(=[O:35])=[O:34])=[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].O>C(#N)C>[OH:7][CH2:8][C@H:9]([CH3:37])[O:10][C:11]1[CH:12]=[C:13]([CH:23]=[C:24]([O:26][C:27]2[CH:32]=[CH:31][C:30]([S:33]([CH3:36])(=[O:34])=[O:35])=[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 3

HCID 962WaterHCID 85247Trimethylsilyl iodideHCID 116195273-[(1S)-2-methoxy-1-methylethoxy]-N-(1-methyl-1H-pyrazol-3-yl)-5-[4-(methylsulfonyl)phenoxy]benzamide

Product 1

HCID 115251163-(((1S)-2-Hydroxy-1-methylethyl)oxy)-N-(1-methyl-1H-pyrazol-3-yl)-5-(4-(methylsulfonyl)phenoxy)benzamideYield 84%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Trimethylsilyl iodide (11.1 mL, 76.3 mmol) was added to a solution of 3-[(1S)-2-methoxy-1-methylethoxy]-N-(1-methyl-1H-pyrazol-3-yl)-5-[4-(methylsulfonyl)phenoxy]benzamide (7.00 g, 15.3 mmol) in dry acetonitrile (100 mL) under argon for 21 h. Water (40 mL) was added to quench the reaction and the acetonitrile was removed in vacuo. The residue was diluted with ethyl acetate-(200 mL) and 1M aqueous hydrochloric acid. The organic layer was separated and further washed with 10% w/v aqueous sodium thiosulfate pentahydrate to remove residual iodine. The organic layer Was separated, dried (MgSO4), filtered and evaporated and purified by column chromatography, eluting with 3% to 5% methanol in DCM, to give the title compound as a white foam (5.70 g, 84%). Recrystallisation from hot ethanol (125 mg/mL) afforded the title compound as colourless needles (87% recovery). Mpt 126-132° C.

Workup

  1. customto quench
  2. customthe reaction
  3. customthe acetonitrile was removed in vacuo
  4. additionThe residue was diluted with ethyl acetate-(200 mL) and 1M aqueous hydrochloric acid
  5. customThe organic layer was separated
  6. washfurther washed with 10% w/v aqueous sodium thiosulfate pentahydrate
  7. customto remove residual iodine
  8. customThe organic layer Was separated
  9. dry with materialdried (MgSO4)
  10. filtrationfiltered
  11. customevaporated
  12. custompurified by column chromatography
  13. washeluting with 3% to 5% methanol in DCM

Sources & evidence

ORD record
ord-22fd2514f4c84eba8a59504b3fabf9ec
Source dataset
uspto-grants-2010_06
Patent number
US07745475B2

Linked notes

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