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

HRID 2247750노트

반응식

HRID 2247750 반응식
[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]

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-e8b78abcc4b243e796e7342763a8125f
출처 데이터셋
uspto-grants-2010_03
특허 번호
US07687491B2

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