Trimethylsilyl iodide → 3-{4-[(Dimethylamino)sulfonyl]phenoxy}-5-[(1S)-2-hydroxy-1-methylethoxy]-N-(1-methyl-1H-pyrazol-3-yl)benzamide

HRID 20542Notes

Reaction equation

HRID 20542 reaction equation
[CH3:1][N:2]([CH3:34])[S:3]([C:6]1[CH:33]=[CH:32][C:9]([O:10][C:11]2[CH:12]=[C:13]([CH:23]=[C:24]([O:26][C@@H:27]([CH3:31])[CH2:28][O:29]C)[CH:25]=2)[C:14]([NH:16][C:17]2[CH:21]=[CH:20][N:19]([CH3:22])[N:18]=2)=[O:15])=[CH:8][CH:7]=1)(=[O:5])=[O:4].I[Si](C)(C)C.C(=O)([O-])O.[Na+]>C(#N)C>[CH3:34][N:2]([CH3:1])[S:3]([C:6]1[CH:7]=[CH:8][C:9]([O:10][C:11]2[CH:12]=[C:13]([CH:23]=[C:24]([O:26][C@@H:27]([CH3:31])[CH2:28][OH:29])[CH:25]=2)[C:14]([NH:16][C:17]2[CH:21]=[CH:20][N:19]([CH3:22])[N:18]=2)=[O:15])=[CH:32][CH:33]=1)(=[O:4])=[O:5]

Participants

5

Reactant 3

HCID 85247Trimethylsilyl iodideHCID 516892Sodium BicarbonateHCID 115983163-{4-[(dimethylamino)sulfonyl]phenoxy}-5-[(1S)-2-methoxy-1-methylethoxy]-N-(1-methyl-1H-pyrazol-3-yl)benzamide

Product 1

HCID 115473993-{4-[(Dimethylamino)sulfonyl]phenoxy}-5-[(1S)-2-hydroxy-1-methylethoxy]-N-(1-methyl-1H-pyrazol-3-yl)benzamideYield 45.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 3-{4-[(dimethylamino)sulfonyl]phenoxy}-5-[(1S)-2-methoxy-1-methylethoxy]-N-(1-methyl-1H-pyrazol-3-yl)benzamide (500 mg, 1.0 mmol) in acetonitrile (30 mL) was added iodotrimethylsilane (0.73 mL, 1.0 g, 5.1 mmol) dropwise. The resulting mixture was stirred at RT for 20 hours. Aqueous sodium hydrogen carbonate solution (saturated, 5 mL) was added slowly and the resulting mixture was concentrated under reduced pressure. Water (50 mL) was added and the mixture was extracted with ethyl acetate (50 mL). The organic layers was washed with brine (50 mL), dried (MgSO4) and evaporated to afford the crude product. This was purified by flash chromatography (eluting with an increasing gradient of 60 to 100% ethyl acetate in isohexane) to afford the pure title compound (216 mg, 45%).

Workup

  1. concentrationthe resulting mixture was concentrated under reduced pressure
  2. additionWater (50 mL) was added
  3. extractionthe mixture was extracted with ethyl acetate (50 mL)
  4. washThe organic layers was washed with brine (50 mL)
  5. dry with materialdried (MgSO4)
  6. customevaporated
  7. customto afford the crude product
  8. customThis was purified by flash chromatography (
  9. washeluting with an increasing gradient of 60 to 100% ethyl acetate in isohexane)

Sources & evidence

ORD record
ord-60a155fcb74746c3abc4c5795b20f29d
Source dataset
uspto-grants-2010_06
Patent number
US07745475B2

Reaction notes

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