Potassium Carbonate → 3-Hydroxy-5-{[(S)-2-hydroxy-1-methylethyl]oxy}-N-(1-methyl-1H-pyrazol-3-yl)benzamide

HRID 20531Notes

Reaction equation

HRID 20531 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:14]=[C:15]([O:17][C@@H:18]([CH3:22])[CH2:19][O:20]C)[CH:16]=1)[C:5]([NH:7][C:8]1[CH:12]=[CH:11][N:10]([CH3:13])[N:9]=1)=[O:6].I[Si](C)(C)C.C(=O)([O-])[O-].[K+].[K+].S([O-])([O-])(=O)=S.[Na+].[Na+]>C(#N)C.CO>[OH:1][C:2]1[CH:3]=[C:4]([CH:14]=[C:15]([O:17][C@@H:18]([CH3:22])[CH2:19][OH:20])[CH:16]=1)[C:5]([NH:7][C:8]1[CH:12]=[CH:11][N:10]([CH3:13])[N:9]=1)=[O:6]

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 24477Sodium ThiosulfateHCID 85247Trimethylsilyl iodideHCID 591271783-hydroxy-5-{[(2S)-1-methoxypropan-2-yl]oxy}-N-(1-methyl-1H-pyrazol-3-yl)benzamide

Product 1

HCID 593468923-Hydroxy-5-{[(S)-2-hydroxy-1-methylethyl]oxy}-N-(1-methyl-1H-pyrazol-3-yl)benzamideYield 74.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6342AcetonitrileSolvent

Procedure

To a solution of 3-hydroxy-5-[(1S)-2-methoxy-(1-methylethyl)oxy]-N-(1-methyl-1H-pyrazol-3-yl)benzamide (10.0 g) in acetonitrile (200 mL), under an atmosphere of argon, was added iodotrimethylsilane (23.8 mL) and the resultant mixture stirred for 16 hours. Methanol (30 mL) was then added and the mixture stirred for 15 minutes, saturated potassium carbonate (30 mL) and sodium thiosulphate (0.5 g) were then added and the mixture stirred for 2 hours. The acetonitrile was removed in vacuo, the residue dissolved in water (150 mL) and continuously extracted with ethyl acetate for 16 hours. The ethyl acetate was removed in vacuo and the residue chromatographed on silica (eluting with 0-5% methanol in ethyl acetate) to give the desired compound (7.1 g).

Workup

  1. stirringthe mixture stirred for 2 hours
  2. customThe acetonitrile was removed in vacuo
  3. dissolutionthe residue dissolved in water (150 mL)
  4. extractioncontinuously extracted with ethyl acetate for 16 hours
  5. customThe ethyl acetate was removed in vacuo
  6. customthe residue chromatographed on silica (eluting with 0-5% methanol in ethyl acetate)

Sources & evidence

ORD record
ord-82c759ae50ae411fa582a449ec7d0704
Source dataset
uspto-grants-2010_06
Patent number
US07745475B2

Reaction notes

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