3-Chlorobenzoic Acid → 2-(Methylsulfonyl)-6-(((triisopropylsilyl)oxy)methyl)nicotinonitrile

HRID 2247750Notes

Reaction equation

HRID 2247750 reaction equation
[CH3:1][S:2][C:3]1[N:10]=[C:9]([CH2:11][O:12][Si:13]([CH:20]([CH3:22])[CH3:21])([CH:17]([CH3:19])[CH3:18])[CH:14]([CH3:16])[CH3:15])[CH:8]=[CH:7][C:4]=1[C:5]#[N:6].ClC1C=C(C=CC=1)C(O)=[O:28].C(=O)([O-])[O-].[K+].[K+].[OH2:39]>C(O)C>[CH3:1][S:2]([C:3]1[N:10]=[C:9]([CH2:11][O:12][Si:13]([CH:17]([CH3:19])[CH3:18])([CH:14]([CH3:16])[CH3:15])[CH:20]([CH3:22])[CH3:21])[CH:8]=[CH:7][C:4]=1[C:5]#[N:6])(=[O:28])=[O:39]

Participants

6

Reactant 4

HCID 4473-Chlorobenzoic AcidHCID 962WaterHCID 11430Potassium CarbonateHCID 685228342-(Methylthio)-6-{[(triisopropylsilyl)oxy]methyl}nicotinonitrile

Product 1

HCID 685269612-(Methylsulfonyl)-6-(((triisopropylsilyl)oxy)methyl)nicotinonitrileYield 100%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 2-(methylthio)-6-{[(triisopropylsilyl)oxy]methyl}nicotinonitrile (1.5 g, 4.5 mmol) that was obtained in Example 24 (24a) in ethanol (10 ml) was added m-chlorobenzoic acid (2.3 g, 14 mmol) at 0° C. with stirring, and after raising the reaction temperature to room temperature, the resulting mixture was stirred for 3 hours and then evaporated in vacuo. Subsequently, to a solution of the residue obtained in ether (20 ml) was added a saturated aqueous solution of potassium carbonate (10 ml) with stirring, and the resulting mixture was stirred for 1 hour. After stirring, the reaction mixture was poured into water (20 ml) and extracted with ether. The extract was washed with a saturated aqueous solution of sodium chloride and dried over magnesium sulfate. After filtration, the filtrate was evaporated in vacuo, and the crude product of the title compound thus obtained was purified by chromatography on a silica gel column using a mixed solvent of ethyl acetate and hexane (2:8 to 3:7) as the eluent to afford the title compound (1.7 g) in a yield of 100% as a white crystalline solid.

Workup

  1. stirringthe resulting mixture was stirred for 3 hours
  2. customevaporated in vacuo
  3. customSubsequently, to a solution of the residue obtained in ether (20 ml)
  4. stirringwith stirring
  5. stirringthe resulting mixture was stirred for 1 hour
  6. stirringAfter stirring
  7. extractionextracted with ether
  8. washThe extract was washed with a saturated aqueous solution of sodium chloride
  9. dry with materialdried over magnesium sulfate
  10. filtrationAfter filtration
  11. customthe filtrate was evaporated in vacuo

Sources & evidence

ORD record
ord-e8b78abcc4b243e796e7342763a8125f
Source dataset
uspto-grants-2010_03
Patent number
US07687491B2

Reaction notes

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