Ethanesulfonamide → N-((5-(3-chloro-4-cyanophenyl)pyridin-3-yl)(cyclopropyl)methyl)ethanesulfonamide

HRID 1897772노트

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HRID 1897772 반응식
[Cl:1][C:2]1[CH:9]=[C:8]([C:10]2[CH:11]=[N:12][CH:13]=[C:14]([CH:16]=O)[CH:15]=2)[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].[CH2:18]([S:20]([NH2:23])(=[O:22])=[O:21])[CH3:19].[CH:24]1([Mg]Br)[CH2:26][CH2:25]1>C1(C)C=CC=CC=1.CC(C)[O-].[Ti+4].CC(C)[O-].CC(C)[O-].CC(C)[O-]>[Cl:1][C:2]1[CH:9]=[C:8]([C:10]2[CH:15]=[C:14]([CH:16]([CH:24]3[CH2:26][CH2:25]3)[NH:23][S:20]([CH2:18][CH3:19])(=[O:22])=[O:21])[CH:13]=[N:12][CH:11]=2)[CH:7]=[CH:6][C:3]=1[C:4]#[N:5]

참가 물질

6

반응물 3

HCID 73702EthanesulfonamideHCID 595783972-Chloro-4-(5-formyl-pyridin-3-yl)-benzonitrileHCID 178418630HCID 178418630, 화합물

생성물 1

HCID 49819978N-((5-(3-chloro-4-cyanophenyl)pyridin-3-yl)(cyclopropyl)methyl)ethanesulfonamide

시약·촉매·용매 2

HCID 11026Titanium isopropoxide촉매HCID 1140Toluene용매

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온도
-40 °C

실험 절차

Titanium(IV) isopropoxide (0.365 mL, 1.245 mmol) was added to a mixture of 2-chloro-4-(5-formylpyridin-3-yl)benzonitrile (as prepared in Example 23, step 1; 0.151 g, 0.622 mmol), ethanesulfonamide (0.085 g, 0.778 mmol) in toluene (10 mL) at room temperature. The resulting mixture was heated to reflux for 4 h. After concentration, the residue was dissolved in THF (5 mL), and cooled to −40° C. Cyclopropylmagnesium bromide (3.73 mL, 1.867 mmol) was added dropwise, and the resulting mixture was slowly warmed up to room temperature and stirred overnight. After quenching by saturated NH4Cl solution, the residue was purified by flash column (ethyl acetate-heptane, v/v, 40%-60%) yielded a slightly yellow solid.

후처리

  1. temperatureThe resulting mixture was heated
  2. temperatureto reflux for 4 h
  3. concentrationAfter concentration
  4. dissolutionthe residue was dissolved in THF (5 mL)
  5. temperaturethe resulting mixture was slowly warmed up to room temperature
  6. customAfter quenching by saturated NH4Cl solution
  7. customthe residue was purified by flash column (ethyl acetate-heptane, v/v, 40%-60%)
  8. customyielded a slightly yellow solid

출처 및 근거

ORD 기록
ord-20d9094c453d48b2ad5a1580a061e8aa
출처 데이터셋
uspto-grants-2013_08
특허 번호
US08519142B2

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